2-(2,6-Dihydroxy-3,5-dichloro-4-methylbenzoyl)-3-methoxy-5-hydroxybenzoic acid methyl ester

Base Information

• Chemical Name: 2-(2,6-Dihydroxy-3,5-dichloro-4-methylbenzoyl)-3-methoxy-5-hydroxybenzoic acid methyl ester
• CAS No.: 2151-16-8
• Molecular Formula: C17H14Cl2O7
• Molecular Weight: 401.2
• Mol file: 2151-16-8.mol

Synonyms:dihydrogedin;Dihydrogeodin;

Chemical Property of 2-(2,6-Dihydroxy-3,5-dichloro-4-methylbenzoyl)-3-methoxy-5-hydroxybenzoic acid methyl ester

Chemical Property:

• PSA: 113.29000
• LogP: 3.44480

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-(2,6-Dihydroxy-3,5-dichloro-4-methylbenzoyl)-3-methoxy-5-hydroxybenzoic acid methyl ester

There total 22 articles about 2-(2,6-Dihydroxy-3,5-dichloro-4-methylbenzoyl)-3-methoxy-5-hydroxybenzoic acid methyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 81.0%

methyl 2-[2,6-bis(methoxymethoxy)-3,5-dichloro-4-methylbenzoyl]-3-methoxy-5-(methoxymethoxy)benzoate (261958-63-8) → methyl 2-(3,5-dichloro-2,6-dihydroxy-4-methylbenzoyl)-5-hydroxy-3-methoxybenzoate (2151-16-8)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; Heating;

DOI:10.1016/S0040-4039(99)02005-5

Reference yield:

1-carbomethoxy-3,5-dihydroxybenzene (2150-44-9) → methyl 2-(3,5-dichloro-2,6-dihydroxy-4-methylbenzoyl)-5-hydroxy-3-methoxybenzoate (2151-16-8)

Guidance literature:

Multi-step reaction with 15 steps

1: 87 percent / DIPEA / CH₂Cl₂ / 5 h / 0 - 20 °C

2: 98 percent / LiAlH₄ / diethyl ether / 2 h / 0 - 20 °C

3: 93 percent / N-bromosuccinimide / dimethylformamide / 2 h / 0 °C

4: 95 percent / NaH / dimethylformamide / 1 h / 0 - 20 °C

5: 95 percent / n-BuLi / hexane; diethyl ether / 3 h / -78 - 20 °C

6: 94 percent / aq. HCl / tetrahydrofuran / 2 h / 20 °C

7: 72 percent / K₂CO₃ / acetone / 1 h / 20 °C

8: 90 percent / Cs₂CO₃ / dimethylformamide / 1 h / 20 °C

9: 86 percent / n-BuLi / tetrahydrofuran; hexane / 3.25 h / -78 - 20 °C

10: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.75 h / 20 °C

11: 79 percent / H₂ / Pd/C / ethanol / 1 h / 20 °C / 760 Torr

12: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

13: aq. NaH₂PO₄; NaClO₂; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol / 1 h / 20 °C

14: 203 mg / diethyl ether; methanol / 0.17 h / 20 °C

15: 81 percent / p-TsOH / methanol / 4 h / Heating

With hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; N-Bromosuccinimide; lithium aluminium tetrahydride; n-butyllithium; 2-methyl-but-2-ene; hydrogen; sodium hydride; potassium carbonate; caesium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; 10: Dess-Martin oxidation / 12: Dess-Martin oxidation;

DOI:10.1016/S0040-4020(01)01250-9

Reference yield:

(2-bromo-3,5-bis(methoxymethoxy)phenyl)methanol (79834-15-4) → methyl 2-(3,5-dichloro-2,6-dihydroxy-4-methylbenzoyl)-5-hydroxy-3-methoxybenzoate (2151-16-8)

Guidance literature:

Multi-step reaction with 12 steps

1: 95 percent / NaH / dimethylformamide / 1 h / 0 - 20 °C

2: 95 percent / n-BuLi / hexane; diethyl ether / 3 h / -78 - 20 °C

3: 94 percent / aq. HCl / tetrahydrofuran / 2 h / 20 °C

4: 72 percent / K₂CO₃ / acetone / 1 h / 20 °C

5: 90 percent / Cs₂CO₃ / dimethylformamide / 1 h / 20 °C

6: 86 percent / n-BuLi / tetrahydrofuran; hexane / 3.25 h / -78 - 20 °C

7: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.75 h / 20 °C

8: 79 percent / H₂ / Pd/C / ethanol / 1 h / 20 °C / 760 Torr

9: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

10: aq. NaH₂PO₄; NaClO₂; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol / 1 h / 20 °C

11: 203 mg / diethyl ether; methanol / 0.17 h / 20 °C

12: 81 percent / p-TsOH / methanol / 4 h / Heating

With hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; hydrogen; sodium hydride; potassium carbonate; caesium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; 7: Dess-Martin oxidation / 9: Dess-Martin oxidation;

DOI:10.1016/S0040-4020(01)01250-9

upstream raw materials:

methyl 2-[2,6-bis(methoxymethoxy)-3,5-dichloro-4-methylbenzoyl]-3-methoxy-5-(methoxymethoxy)benzoate

orcinol

1-carbomethoxy-3,5-dihydroxybenzene

4,6-dichloro-5-methylresorcinol

Downstream raw materials:

5-acetoxy-2-(2,6-diacetoxy-3,5-dichloro-4-methyl-benzoyl)-3-methoxy-benzoic acid methyl ester

4,6-dichloro-5-methylresorcinol

(+)-geodin

3,5-dichloro-2,6-dihydroxy-4-methyl-benzoic acid

Refernces

• 1、 Katoh, Tadashi,Ohmori, Osamu. "Studies toward the total synthesis of Sch 202596, an antagonist of the galanin receptor subtype GalR1: Synthesis of geodin, the spirocoumaranone subunit of Sch 202596". . p. 465 - 469. Retrieved 2007/10/03.