(R)-α-(Hydroxymethyl)benzeneacetic acid methyl ester

Base Information

• Chemical Name: (R)-α-(Hydroxymethyl)benzeneacetic acid methyl ester
• CAS No.: 20731-95-7
• Molecular Formula: C10H12O3
• Molecular Weight: 180.203
• Mol file: 20731-95-7.mol

Synonyms:2-hydroxy-2-phenylpropionic acid methyl ester;(+/-)-methyl 2-hydroxy-2-phenylpropionate;methyl 2-hydroxy-2-phenylpropanoate;methyl D-phenyllactate;methyl 2-hydroxy-2-phenylpropionate;methyl L-phenyllactate;

Chemical Property of (R)-α-(Hydroxymethyl)benzeneacetic acid methyl ester

Chemical Property:

• Boiling Point: 127.5 °C(Press: 18 Torr)
• PKA: 12.26±0.29(Predicted)
• PSA: 46.53000
• Density: 1.146±0.06 g/cm3(Predicted)
• LogP: 1.06710
• Storage Temp.: Sealed in dry,Room Temperature

Purity/Quality:

99%, ^*data from raw suppliers

methyl2-hydroxy-2-phenylpropanoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (R)-α-(Hydroxymethyl)benzeneacetic acid methyl ester

There total 101 articles about (R)-α-(Hydroxymethyl)benzeneacetic 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: 97.0%

2-phenyllactic acid (515-30-0) + methyl iodide (74-88-4) → methyl 2-hydroxy-2-phenylpropanoate (20731-95-7)

Guidance literature:

With potassium carbonate; In acetone; Heating;

DOI:10.1016/j.tetasy.2003.05.001

Reference yield: 95.0%

methyl 2-phenyl-2-(tetrahydropyranyloxy)propanoate (131490-20-5) → (S)-methyl atrolactate (13448-81-2,20731-95-7,67596-42-3,13448-80-1)

Guidance literature:

With hydrogenchloride; In methanol; water; for 1h;

DOI:10.1021/jo00003a035

Reference yield: 94.0%

methanol (67-56-1) + 2-phenyllactic acid (515-30-0) → methyl 2-hydroxy-2-phenylpropanoate (20731-95-7)

Guidance literature:

With toluene-4-sulfonic acid; at 75 ℃; for 6h;

upstream raw materials:

(S)-Atrolactic acid

diazomethane

(S)-2-hydroxy-2-phenylbutanoic acid

methanol

Downstream raw materials:

2-hydroxy-N,2-diphenylpropanamide

(R)-1.1.2-triphenyl-propanediol-(1.2)

(R)-Atrolactinsaeureamid

(S)-methyl atrolactate

Refernces

• 1、 Stankovic, Sasa,Espenson, James H.. "Oxidation of Methyl Trimethylsilyl Ketene Acetals to α-Hydroxyesters with Urea Hydrogen Peroxide Catalyzed by Methyltrioxorhenium". . p. 5528 - 5530. Retrieved 2000.
• 2、 Kodama, Koichi,Nagata, Jun,Kurozumi, Nobuhiro,Shitara, Hiroaki,Hirose, Takuji. "Solvent-induced chirality switching in the enantioseparation of regioisomeric hydroxyphenylpropionic acids via diastereomeric salt formation with (1R,2S)-2-amino-1,2-diphenylethanol". supporting information. p. 460 - 466. Retrieved 2017/03/23.
• 3、 Shibatomi, Kazutaka,Kitahara, Kazumasa,Okimi, Takuya,Abe, Yoshiyuki,Iwasa, Seiji. "Enantioselective fluorination of α-branched aldehydes and subsequent conversion to α-hydroxyacetals via stereospecific C-F bond cleavage". . p. 1388 - 1392. Retrieved 2016/02/05.