15462-91-6

Basic information

• Product Name: 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one
• Synonyms: 3-[2-(3,4-Dimethoxybenzoyl)-4,5-dimethoxyphenyl]-2-pentanone;3-[2-(3,4-Dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one;Benzophenone, 2-(1-ethylacetonyl)-3',4,4',5-tetramethoxy-;Einecs 239-479-8;Care Fexofenadine Pan interMediates, 3 - (2 - (3,4-DiMethoxybenzoyl)-4,5-diMethoxyphenyl) pentan-2-one;2-Pentanone,3-[2-(3,4-diMethoxybenzoyl)-4,5-diMethoxyphenyl]-;3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one 3-[2-(3,4-Dimethoxybenzoyl)-4,5-dimethoxyphenyl]-2-pentanone;Tofisopam intermediate
• CAS NO: 15462-91-6
• Molecular Formula: C₂₂H₂₆O₆
• Molecular Weight: 386.44
• EINECS: 239-479-8
• Product Categories: (intermediate of tofisopam)
• Mol File: 15462-91-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: 156-157 °C
• Boiling Point: 552.7°Cat760mmHg
• Flash Point: 239.8°C
• Appearance: /
• Density: 1.124g/cm³
• Vapor Pressure: 2.91E-12mmHg at 25°C
• Refractive Index: 1.53
• CAS DataBase Reference: 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one(15462-91-6)
• EPA Substance Registry System: 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one(15462-91-6)

Safety Data

• Hazardous Substances Data: 15462-91-6(Hazardous Substances Data)

Usage

General Description

3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethylphenyl]pentan-2-one is a chemical compound. The detailed structural specification suggests that it has multiple functional groups, including a pentan-2-one, or a pentanone, which is a type of ketone; a 3,4-dimethoxybenzoyl, which suggests a benzoic acid ester derivative with two methoxy groups; and a 4,5-dimethylphenyl, which is a phenyl group substituted with two methyl groups. It's not a common or widely-used chemical, and as such, there’s limited information available about its properties, uses, or safety. Therefore, any handling or use of it should be done with utmost caution, preferably under the guidance of a trained professional. It falls in the scientific realm of organic chemistry--the study of structures, properties, composition, reactions, and synthesis of organic compounds consisting of carbon atoms.

InChI:InChI=1/C22H26O6/c1-7-15(13(2)23)16-11-20(27-5)21(28-6)12-17(16)22(24)14-8-9-18(25-3)19(10-14)26-4/h8-12,15H,7H2,1-6H3

Synthetic route

C24H34O6 → 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6)

Conditions	Yield
With silica gel In dichloromethane; sulfuric acid for 2h;	93%

1-(3,4-dimethoxy-phenyl)-3-ethyl-5,6-dimethoxy-2-methyl-indane (4483-47-0) → 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6)

Conditions	Yield
With hydrogenchloride; dihydrogen peroxide; acetic acid; copper(II) oxide In water at 3 - 25℃; for 10h; Reagent/catalyst; Temperature;	88.2%

1-(3,4-dimethoxyphenyl)-6,7-dimethoxy-4-ethyl-3-methylisochroman (2029-86-9) → 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6) + 2-(3,4-dimethoxybenzoyl)-4,5-dimethoxypropiophenone (102719-50-6)

Conditions	Yield
With chromium(VI) oxide; sulfuric acid In water; acetone for 2h; Ambient temperature;	A 48% B 24%

{4,5-dimethoxy-2-[1-(2-methyl-[1,3]dioxolan-2-yl)propyl]phenyl}(3,4-dimethoxyphenyl)methanone → 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6)

Conditions	Yield
With sulfuric acid In dichloromethane at 20℃; for 2h;	32%

diazomethane (186581-53-3, 908094-01-9) + 2-(1-ethyl-2-oxo-propyl)-5,4'-dihydroxy-4,3'-dimethoxy-benzophenone → 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6)

Conditions	Yield
With methanol

1-ethyl-3-(3,4-dimethoxy-phenyl)-5,6-dimethoxy-2-methyl-indene (82005-37-6) → 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6)

Conditions	Yield
With chromium(VI) oxide; acetic acid

1-(3,4-dimethoxyphenyl)-6,7-dimethoxy-4-ethyl-3-methylisochroman (2029-86-9) + acetic acid (64-19-7) + chromium (VI)-oxide → 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6)

5.6-dimethoxy-2t-methyl-1r-ethyl-3c-<3.4-dimethoxy-phenyl>-indan → 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6)

Conditions	Yield
With chromium(VI) oxide; acetic acid

(+-)-1r-ethyl-3c-(3,4-dimethoxy-phenyl)-5,6-dimethoxy-2t-methyl-indan (4483-47-0, 15161-79-2, 22688-51-3, 22688-52-4, 22688-53-5, 62211-17-0) + acetic acid (64-19-7) + CrO3 (2 mol) → 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6)

Conditions	Yield
at 15 - 20℃;

(+-)-1r-ethyl-3c-(3,4-dimethoxy-phenyl)-5,6-dimethoxy-2t-methyl-indan (4483-47-0, 15161-79-2, 22688-51-3, 22688-52-4, 22688-53-5, 62211-17-0) + acetic acid (64-19-7) + CrO3 (3.3 mol) → 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6) + 2-(3,4-Dimethoxy-benzoyl)-4,5-dimethoxy-benzoic acid (7249-36-7) + Veratric acid (93-07-2)

Conditions	Yield
at 15 - 20℃;

3,4-dimethoxy-benzaldehyde (120-14-9) → 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 92 percent / HCl gas / dioxane / 1 h / Heating 2: 48 percent / chromium trioxide, 35percent H2SO4 / acetone; H2O / 2 h / Ambient temperature View Scheme

3-(3,4-dimethoxyphenyl)pentan-2-one → 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium borohydride 2: 92 percent / HCl gas / dioxane / 1 h / Heating 3: 48 percent / chromium trioxide, 35percent H2SO4 / acetone; H2O / 2 h / Ambient temperature View Scheme

3-(3,4-dimethoxyphenyl)-2-pentanol (102728-10-9) → 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 92 percent / HCl gas / dioxane / 1 h / Heating 2: 48 percent / chromium trioxide, 35percent H2SO4 / acetone; H2O / 2 h / Ambient temperature View Scheme

2-ethyl-1-(3,4-dimethoxyphenyl)butan-1,3-dione + 4,5-dimethoxy-2-(trimethylsilyl)phenyl trifluoromethanesulfonate → 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6)

Conditions	Yield
With cesium fluoride In acetonitrile at 60℃; for 10h;

2-methoxy-4-propenylphenol (97-54-1) → 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: sulfuric acid / methanol / 2 h / Reflux 2: sodium hydroxide / methanol 3: hydrogenchloride; dihydrogen peroxide; copper(II) oxide; acetic acid / water / 10 h / 3 - 25 °C View Scheme

3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6) + toluene-4-sulfonic acid hydrazide (1576-35-8) → 4-Ethyl-6,7-dimethoxy-1-(3,4-dimethoxyphenyl)-3-methylisoquinoline-N-p-toluenesulphonylimine (98352-06-8)

Conditions	Yield
hydrogenchloride In ethanol for 0.333333h; Heating;	85%

3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6) + benzoic acid hydrazide (613-94-5) → 4-Ethyl-6,7-dimethoxy-1-(3,4-dimethoxyphenyl)-3-methylisoquinoline-N-benzoylimine (98352-07-9)

Conditions	Yield
hydrogenchloride In ethanol for 0.333333h; Heating;	63%

3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6) → tofisopam (22345-47-7, 914303-48-3, 914303-49-4, 914303-50-7, 914303-51-8)

Conditions	Yield
With hydrazine hydrate In ethanol for 1h; Heating;	60%
Stage #1: 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one With hydrogenchloride; hydrazine hydrate; acetic acid In methanol; water at 20 - 27℃; for 2h; Stage #2: With ammonium hydroxide In water for 1h;

3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6) + nitric acid (7697-37-2) + acetic acid (64-19-7) → 2,3,6,7-tetramethoxy-9,10-anthraquinone (5629-55-0) + 2-(3,4-Dimethoxy-benzoyl)-4,5-dimethoxy-benzoic acid (7249-36-7)

3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6) + aq.-ethanolic NaOH → 1-ethyl-4-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-[2]naphthol (15462-94-9)

3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6) + nitric acid (7697-37-2) + acetic acid (64-19-7) → 10-acetyl-2,3,6,7-tetramethoxy-anthrone (740836-53-7)

Conditions	Yield
Erwaermen der mit Wasser verduennten Reaktionsloesung;

3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6) + mineral acid → 6.7-dimethoxy-3-methyl-4-ethyl-1-<3.4-dimethoxy-phenyl>-isochromenylium salts

3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6) → 3-acetyl-1-(3,4-dimethoxyphenyl)-7,8-dimethoxy-5-ethyl-4-methyl-3H-2,3-benzodiazepine (90140-50-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 60 percent / hydrazin hydrate 98percent / ethanol / 1 h / Heating 2: 64 percent / 3 h / Heating View Scheme

3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6) → 3-Acetyl-1-(3,4-dimethoxyphenyl)-5-ethyl-4,5-dihydro-7,8-dimethoxy-4-methylen-3H-2,3-benzodiazepin (54080-15-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 60 percent / hydrazin hydrate 98percent / ethanol / 1 h / Heating 2: 20 percent / 3 h / Heating View Scheme

3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6) → 1-(3,4-dimethoxyphenyl)-7,8-dimethoxy-5-ethyl-4-methyl-3,4-dihydro-5H-2,3-benzodiazepine

Conditions	Yield
Multi-step reaction with 2 steps 1: 60 percent / hydrazin hydrate 98percent / ethanol / 1 h / Heating 2: 82 percent / sodium borohydride / methanol / 2 h / Ambient temperature View Scheme

3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6) → 2,3,6,7-tetramethoxy-9,10-anthraquinone (5629-55-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid; nitric acid / und Erwaermen der mit Wasser versetzten Reaktionsloesung 2: acetic acid; nitric acid / 100 °C View Scheme

Upstream product

• 4483-47-0 1-(3,4-dimethoxy-phenyl)-3-ethyl-5,6-dimethoxy-2-methyl-indane 
• 97-54-1 2-methoxy-4-propenylphenol 
• 866252-52-0 4,5-dimethoxy-2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 102728-10-9 3-(3,4-dimethoxyphenyl)-2-pentanol 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 4483-47-0 (+-)-1r-ethyl-3c-(3,4-dimethoxy-phenyl)-5,6-dimethoxy-2t-methyl-indan 
• 64-19-7 acetic acid 
• 2029-86-9 1-(3,4-dimethoxyphenyl)-6,7-dimethoxy-4-ethyl-3-methylisochroman 
• 82005-37-6 1-ethyl-3-(3,4-dimethoxy-phenyl)-5,6-dimethoxy-2-methyl-indene 
• 186581-53-3 diazomethane 

Downstream Products

• 22345-47-7 tofisopam 
• 15462-94-9 1-ethyl-4-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-[2]naphthol 
• 54080-15-8 3-Acetyl-1-(3,4-dimethoxyphenyl)-5-ethyl-4,5-dihydro-7,8-dimethoxy-4-methylen-3H-2,3-benzodiazepin 
• 90140-50-4 3-acetyl-1-(3,4-dimethoxyphenyl)-7,8-dimethoxy-5-ethyl-4-methyl-3H-2,3-benzodiazepine 
• 5629-55-0 2,3,6,7-tetramethoxy-9,10-anthraquinone 
• 7249-36-7 2-(3,4-Dimethoxy-benzoyl)-4,5-dimethoxy-benzoic acid 
• 98352-06-8 4-Ethyl-6,7-dimethoxy-1-(3,4-dimethoxyphenyl)-3-methylisoquinoline-N-p-toluenesulphonylimine 
• 114920-22-8 4-ethyl-1-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-3-methyl-isoquinoline-2-oxide 
• 1616-49-5 4-ethyl-3-methyl-6,7-dimethoxy-1-(3,4-dimethoxyphenyl)isoquinoline 

Relevant articles and documents

holds the non-rope to divide method for the preparation of intermediates

The invention relates to a preparation method of a tofisopam intermediate 3-[2-(3,4-dimethoxy benzoic acyl)-4,5-dimethoxyphenyl]-penta-2-ketone, and belongs to the technical field of pharmaceutical synthesis. The method comprises the following step: carrying out reaction on 1-(3,4-dimethoxy-phenyl)-3-ethyl-5,6-dimethoxy-2-methyl-indan as an initial material, copper compounds as catalysts, and hydrogen peroxide as an oxidant under an acid condition, so as to prepare the tofisopam intermediate 3-[2-(3,4-dimethoxy benzoic acyl)-4,5-dimethoxyphenyl]-penta-2-ketone. According to the preparation method, the content of heavy metals in the wastewater is greatly lowered, chromium compounds with carcinogenesis are avoided, the production capacity of tofisopam is released, and the environment is protected.

PROCESS FOR THE PREPARATION OF 3-[2-(3,4-DIMETHOXYBENZOYL)-4,5- DIMETHOXYPHENYL] -PENTAN-2-ONE

The invention relates to a new process for the preparation of 3-[2-(3,4-dimethoxybenzoyl)-4,5- dimethoxyphenyl]-pentan-2-one of the formula (I), starting from a compound of the general formula (II) and subjecting the thus-obtained compound of the general formula (IV) to hydrolysis. The compound of the formula (I) is a pharmaceutical intermediate, which can be used for the preparation of an anxiolytic, namely tofisopam (INN).

Derivatives of 2,3-benzodiazepine

-