α-Hydroxy-4-acetoxybenzenepropionic acid methyl ester

Base Information

• Chemical Name: α-Hydroxy-4-acetoxybenzenepropionic acid methyl ester
• CAS No.: 77573-21-8
• Molecular Formula: C12H14O5
• Molecular Weight: 0
• Mol file: 77573-21-8.mol

Synonyms:3-[4-(Acetyloxy)phenyl]-2-hydroxypropionic acid methyl ester;α-Hydroxy-4-acetoxybenzenepropionic acid methyl ester

Chemical Property of α-Hydroxy-4-acetoxybenzenepropionic acid methyl ester

Chemical Property:

• PSA: 72.83000
• LogP: 0.68830

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of α-Hydroxy-4-acetoxybenzenepropionic acid methyl ester

There total 4 articles about α-Hydroxy-4-acetoxybenzenepropionic 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: 98.0%

methyl 3-p-acetoxyphenyl-2-t-butyldimethylsiloxy propionate (864070-64-4) → methyl 3-p-acetoxyphenyl-2-hydroxy propionate (77573-21-8)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran;

DOI:10.1016/j.tet.2005.06.022

Reference yield:

methyl 3-p-benzyloxyphenyl-2-t-butyldimethylsiloxy propionate (481072-85-9) → methyl 3-p-acetoxyphenyl-2-hydroxy propionate (77573-21-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / hydrogen / Pd/C / ethyl acetate

2: 88 percent / pyridine

3: 98 percent / tetra-n-butylammonium fluoride; acetic acid / tetrahydrofuran

With pyridine; tetrabutyl ammonium fluoride; hydrogen; acetic acid; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate;

DOI:10.1016/j.tet.2005.06.022

Reference yield:

(+/-)-methyl 3-p-benzyloxyphenyl-2-hydroxypropionate (128316-64-3,481072-37-1) → methyl 3-p-acetoxyphenyl-2-hydroxy propionate (77573-21-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / imidazole; 4-(dimethylamino)pyridine / dimethylformamide

2: 87 percent / hydrogen / Pd/C / ethyl acetate

3: 88 percent / pyridine

4: 98 percent / tetra-n-butylammonium fluoride; acetic acid / tetrahydrofuran

With pyridine; 1H-imidazole; dmap; tetrabutyl ammonium fluoride; hydrogen; acetic acid; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2005.06.022

upstream raw materials:

methyl 3-p-acetoxyphenyl-2-t-butyldimethylsiloxy propionate

methyl 3-p-hydroxyphenyl-2-t-butyldimethylsiloxy propionate

methyl 3-p-benzyloxyphenyl-2-t-butyldimethylsiloxy propionate

(+/-)-methyl 3-p-benzyloxyphenyl-2-hydroxypropionate

Downstream raw materials:

methyl 2-(6'-O-benzyl-2',3',4'-tri-O-t-butyldimethylsilyl-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsiloxyphenyl propionate

methyl 2-(6'-O-acetyl-2',3',4'-tri-O-t-butyldimethylsilyl-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsiloxyphenyl propionate

methyl 2-(2',3',4'-tri-O-t-butyldimethylsilyl-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsiloxyphenyl propionate

methyl 2-(6'-O-benzyl-β-D-galactopyranosyloxy)-3-p-hydroxyphenyl propionate

Refernces