Benzenepropanoic acid, -alpha--[(acetyloxy)methyl]- (9CI)

Base Information

• Chemical Name: Benzenepropanoic acid, -alpha--[(acetyloxy)methyl]- (9CI)
• CAS No.: 187610-68-0
• Molecular Formula: C12H14 O4
• Molecular Weight: 222.241
• Mol file: 187610-68-0.mol

Synonyms:2-Acetoxymethyl-3-phenylpropionicacid

Chemical Property of Benzenepropanoic acid, -alpha--[(acetyloxy)methyl]- (9CI)

Chemical Property:

• PSA: 63.60000
• LogP: 1.49300

Purity/Quality:

99% ^*data from raw suppliers

Benzenepropanoicacid,α-[(acetyloxy)methyl]- ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Benzenepropanoic acid, -alpha--[(acetyloxy)methyl]- (9CI)

There total 3 articles about Benzenepropanoic acid, -alpha--[(acetyloxy)methyl]- (9CI) 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: 86.0%

(RS)-2-hydroxymethyl-3-phenylpropionic acid (6811-98-9) + acetyl chloride (75-36-5) → (+/-)-α-<(acetoxy)methyl>benzenepropanoic acid (187610-68-0)

Guidance literature:

In tetrahydrofuran; for 48h; Ambient temperature;

DOI:10.1021/jm00086a017

Reference yield: 73.0%

rac-2-hydroxymethyl-3-phenyl-propyl acetate (90107-01-0) → (+/-)-α-<(acetoxy)methyl>benzenepropanoic acid (187610-68-0)

Guidance literature:

With jones' reagent; In acetone;

DOI:10.1016/S0968-0896(02)00108-6

Reference yield:

3-Phenylpropionic acid (501-52-0) → (+/-)-α-<(acetoxy)methyl>benzenepropanoic acid (187610-68-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) diisopropyl amine, n-butyllithium / 1.) THF, hexane, 20 deg C, 15 min, 2.) THF, hexane, 5-15 deg C, 10 h

2: 86 percent / tetrahydrofuran / 48 h / Ambient temperature

With n-butyllithium; diisopropylamine; In tetrahydrofuran;

DOI:10.1021/jm00086a017

upstream raw materials:

(RS)-2-hydroxymethyl-3-phenylpropionic acid

acetyl chloride

rac-2-hydroxymethyl-3-phenyl-propyl acetate

3-Phenylpropionic acid

Downstream raw materials:

(RS)-2-hydroxymethyl-3-phenylpropionic acid

methyl 3-acetoxy-2-benzylpropanoate

(2S,1'R)-2-acetoxymethyl-3-phenyl-N-(1'-phenylethyl)propionamide

(2R,1'R)-2-acetoxymethyl-3-phenyl-N-(1'-phenylethyl)propionamide

Refernces

• 1、 Fincham, Christopher I.,Higginbottom, Michael,Hill, David R.,Horwell, David C.,O'Toole, John C,et al.. "Amide Bond Replacements Incorporated into CCK-B Selective "Dipeptoids"". . p. 1472 - 1484. Retrieved 2007/10/02.