5-Formylbenzo[1,3]dioxole-4-carboxylic acid ethyl ester

Base Information

• Chemical Name: 5-Formylbenzo[1,3]dioxole-4-carboxylic acid ethyl ester
• CAS No.: 75267-17-3
• Molecular Formula: C11H10O5
• Molecular Weight: 222.197
• Hs Code.: 2932999099
• DSSTox Substance ID: DTXSID00446863
• Wikidata: Q72479195
• Mol file: 75267-17-3.mol

Synonyms:75267-17-3;5-FORMYLBENZO[1,3]DIOXOLE-4-CARBOXYLIC ACID ETHYL ESTER;ethyl 5-formyl-1,3-benzodioxole-4-carboxylate;5-formyl-benzo[1,3]dioxole-4-carboxylic acid ethyl ester;1,3-Benzodioxole-4-carboxylicacid, 5-formyl-, ethyl ester;Ethyl 5-formyl-2H-1,3-benzodioxole-4-carboxylate;Ethyl 5-formylbenzo[d][1,3]dioxole-4-carboxylate;DTXSID00446863;FT-0764360

Chemical Property of 5-Formylbenzo[1,3]dioxole-4-carboxylic acid ethyl ester

Chemical Property:

• Vapor Pressure: 4.36E-06mmHg at 25°C
• Refractive Index: 1.581
• Boiling Point: 383.6 °C at 760 mmHg
• Flash Point: 228.1 °C
• PSA: 61.83000
• Density: 1.333 g/cm³
• LogP: 1.40450
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 222.05282342
• Heavy Atom Count: 16
• Complexity: 278

Purity/Quality:

98%Min ^*data from raw suppliers

5-FORMYLBENZO[1,3]DIOXOLE-4-CARBOXYLIC ACID ETHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(C=CC2=C1OCO2)C=O

Technology Process of 5-Formylbenzo[1,3]dioxole-4-carboxylic acid ethyl ester

There total 1 articles about 5-Formylbenzo[1,3]dioxole-4-carboxylic acid ethyl 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:

N-(3,4-methylenedioxybenzylidene)-N-cyclohexylamine (58343-42-3) + chloroformic acid ethyl ester (541-41-3) → 5-Formyl-benzo[1,3]dioxole-4-carboxylic acid ethyl ester (75267-17-3)

Guidance literature:

With n-butyllithium; Yield given. Multistep reaction; 1.) THF, hexane, -78 deg C, 3 h 2.) -78 deg C to 23 deg C, 4 h;

DOI:10.1021/jo01313a011

Reference yield:

5-Formyl-benzo[1,3]dioxole-4-carboxylic acid ethyl ester (75267-17-3) → (+/-)-chelidonine (20267-87-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 84 percent / H₂, / 10percent Pd/C / ethanol / 1396.3 - 2585.7 Torr

2: 74 percent / SOCl₂, / CH₂Cl₂ / 2.25 h / 23 °C

3: 72 percent / dimethylsulfoxide / 12 h / 23 °C

4: 92 percent / (aq) KOH / 3 h / Heating

5: 96 percent / AcCl / 6 h / Heating

6: 62 percent / acetonitrile / 1 h / Heating

8: 19 percent / CF₃COOH / 0.02 h / 0 °C

9: LiAlH₄, 15percent NaOH / 1.) THF, reflux, 17 h 2.) 0 deg C, 20 min, water

With potassium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; thionyl chloride; hydrogen; acetyl chloride; trifluoroacetic acid; palladium on activated charcoal; In ethanol; dichloromethane; dimethyl sulfoxide; acetonitrile;

DOI:10.1021/jo01313a011

Reference yield:

5-Formyl-benzo[1,3]dioxole-4-carboxylic acid ethyl ester (75267-17-3) → 4-Benzyloxymethyl-benzo[1,3]dioxole-5-carbaldehyde (219474-53-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 99 percent / BF₃*Et₂O / acetic acid / 12 h / Ambient temperature

2: 91 percent / LiAlH₄ / tetrahydrofuran / 18 h / Ambient temperature

3: 91 percent / NaH, TBA / tetrahydrofuran / 25 h / Ambient temperature

4: 99 percent / (CF₃CO₂)2IPh / acetonitrile; H₂O / Ambient temperature

With lithium aluminium tetrahydride; boron trifluoride diethyl etherate; sodium hydride; tert-butylamine; bis-[(trifluoroacetoxy)iodo]benzene; In tetrahydrofuran; water; acetic acid; acetonitrile;

upstream raw materials:

N-(3,4-methylenedioxybenzylidene)-N-cyclohexylamine

chloroformic acid ethyl ester

Downstream raw materials:

decumbenine B

4-Benzyloxymethyl-benzo[1,3]dioxole-5-carbaldehyde

4-Benzyloxymethyl-5-[1,3]dithian-2-yl-benzo[1,3]dioxole

Benzyl-[1-(4-benzyloxymethyl-benzo[1,3]dioxol-5-yl)-meth-(E)-ylidene]-amine

Refernces

• 1、 Cushman, Mark,Choong, Tung-Chung,Valko, Joseph T.,Koleck, Mary P.. "Total Synthesis of (+/-)-Chelidonine". . p. 5067 - 5073. Retrieved 2007/10/02.