Acetic acid, [(3,4-dimethoxyphenyl)methoxy]-, methyl ester

Base Information

• Chemical Name: Acetic acid, [(3,4-dimethoxyphenyl)methoxy]-, methyl ester
• CAS No.: 185300-91-8
• Molecular Formula: C12H16O5
• Molecular Weight: 240.256
• DSSTox Substance ID: DTXSID60445433
• Wikidata: Q82263829
• Mol file: 185300-91-8.mol

Synonyms:185300-91-8;Acetic acid, [(3,4-dimethoxyphenyl)methoxy]-, methyl ester;DTXSID60445433

Chemical Property of Acetic acid, [(3,4-dimethoxyphenyl)methoxy]-, methyl ester

Chemical Property:

• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 240.09977361
• Heavy Atom Count: 17
• Complexity: 231

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)COCC(=O)OC)OC

Technology Process of Acetic acid, [(3,4-dimethoxyphenyl)methoxy]-, methyl ester

There total 1 articles about Acetic acid, [(3,4-dimethoxyphenyl)methoxy]-, 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: 98.0%

glycolic acid methyl ester (96-35-5) + (3,4-dimethoxoxyphenyl)methyl 2,2,2-trichloroacetimidate (905589-59-5) → (3,4-Dimethoxy-benzyloxy)-acetic acid methyl ester (185300-91-8)

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane; for 36h;

DOI:10.1021/jo961841k

Reference yield: 96.0%

(3,4-Dimethoxy-benzyloxy)-acetic acid methyl ester (185300-91-8) → (3,4-dimethoxybenzyloxy) acetic acid (933731-96-5)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; for 0.5h;

DOI:10.1021/jo961841k

Reference yield:

(3,4-Dimethoxy-benzyloxy)-acetic acid methyl ester (185300-91-8) → (S)-(3,4-Dimethoxy-benzyloxy)-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-acetic acid methyl ester (185300-82-7)

Guidance literature:

Multi-step reaction with 11 steps

1: 96 percent / aq. NaOH / tetrahydrofuran / 0.5 h

2: 1.) n-BuLi, 2.) oxalyl chloride / 1.) THF, hexanes, -78 deg C, 10 min, 2.) THF, hexanes, 23 deg C, 1 h

3: 62 percent / n-BuLi / tetrahydrofuran / 0.58 h / -78 °C

4: 1.) Bu₂BOTf, Et₃N / 1.) CH₂Cl₂, -78 deg C - 3 h, 0 deg C - 30 min, 2.) CH₂Cl₂, -78 deg C - 3 h, 0 deg C - 30 min

5: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, -78 -> 0 deg C

6: H₂ / Pd/C / methanol / 24 h / Ambient temperature

7: camphorsulfonic acid / methanol / 8 h

8: 1.) COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, -78 deg C -> 0 deg C

10: 82 percent / aq. H₂O₂, LiOH / tetrahydrofuran / 11 h / 23 °C

11: 71 percent / tetrahydrofuran; methanol; hexane

With lithium hydroxide; sodium hydroxide; n-butyllithium; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; hydrogen; dihydrogen peroxide; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane;

DOI:10.1021/jo961841k

upstream raw materials:

glycolic acid methyl ester

(3,4-dimethoxoxyphenyl)methyl 2,2,2-trichloroacetimidate

Downstream raw materials:

(3,4-dimethoxybenzyloxy) acetic acid

7-(3,4-dimethoxybenzyl)pederic acid

(S)-(3,4-Dimethoxy-benzyloxy)-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-acetic acid methyl ester

(3,4-Dimethoxy-benzyloxy)-acetyl chloride