3-Acetoxy-2-benzylpropanoic acid

Base Information

• Chemical Name: 3-Acetoxy-2-benzylpropanoic acid
• CAS No.: 187610-68-0
• Molecular Formula: C12H14 O4
• Molecular Weight: 222.241
• DSSTox Substance ID: DTXSID701268294
• Mol file: 187610-68-0.mol

Synonyms:187610-68-0;3-Acetoxy-2-benzylpropanoic acid;Benzenepropanoic acid, -alpha--[(acetyloxy)methyl]- (9CI);2-(acetyloxymethyl)-3-phenylpropanoic acid;3-(2-(Acetoxymethyl)phenyl)propanoic acid;SCHEMBL8701664;DTXSID701268294;CS-M1745;WEA23285;AKOS027401341;CS-13428;3-(ACETYLOXY)-2-BENZYLPROPANOIC ACID;alpha-[(Acetyloxy)methyl]benzenepropanoic acid

Chemical Property of 3-Acetoxy-2-benzylpropanoic acid

Chemical Property:

• PSA: 63.60000
• LogP: 1.49300
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 222.08920892
• Heavy Atom Count: 16
• Complexity: 243

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:

• Canonical SMILES: CC(=O)OCC(CC1=CC=CC=C1)C(=O)O

Technology Process of 3-Acetoxy-2-benzylpropanoic acid

There total 3 articles about 3-Acetoxy-2-benzylpropanoic acid 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:

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

tricyclo<3.3.1.1^3,7>dec-2-yl (+/-)-<1-<<2-(hydroxymethyl)-1-oxo-3-phenylpropyl>amino>-2-(1H-indol-3-yl)ethyl>carbamate

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.