32174-38-2

Basic information

• Product Name: methyl (R)-2-hydroxy-2-(4-methoxyphenyl)acetate
• Synonyms: methyl (R)-2-hydroxy-2-(4-methoxyphenyl)acetate
• CAS NO: 32174-38-2
• Molecular Weight: 196.203
• Mol File: 32174-38-2.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: methyl (R)-2-hydroxy-2-(4-methoxyphenyl)acetate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (R)-2-hydroxy-2-(4-methoxyphenyl)acetate(32174-38-2)
• EPA Substance Registry System: methyl (R)-2-hydroxy-2-(4-methoxyphenyl)acetate(32174-38-2)

Safety Data

• Hazardous Substances Data: 32174-38-2(Hazardous Substances Data)

Upstream product

• 32766-61-3 4-methoxyphenylglyoxylate methyl ester 
• 123-11-5 4-methoxy-benzaldehyde 
• 13305-14-1 methyl 2-hydroxy-2-(4-methoxyphenyl)acetate 
• 20714-90-3 4-Methoxymandelic acid 
• 108-05-4 vinyl acetate 
• 33646-40-1 4-methoxymandelonitrile 
• 120390-76-3 (R)-(+)-α-<(tert-butyldimethylsilyl)oxy>-4-methoxybenzeneacetonitrile 
• 97070-73-0 (R)-(+)-α-Hydroxy-4-methoxybenzeneacetonitrile 
• 67-56-1 methanol 
• 7677-24-9 trimethylsilyl cyanide 
• 186581-53-3 diazomethane 
• 20714-89-0 (R)-2-hydroxy-2-(4-methoxyphenyl)acetic acid 
• 74-88-4 methyl iodide 
• 55538-79-9 methyl (+/-)-α-acetoxy-α-(4-methoxyphenyl)acetate 

Downstream Products

• 20714-89-0 (R)-2-hydroxy-2-(4-methoxyphenyl)acetic acid 
• 130718-65-9 (R)-3-(4-methoxyphenyl)-1,1-bis(p-tolylthio)-3-(trimethylsilyloxy)propan-2-one 
• 130718-74-0 (4R,5R)-cis-4--5-(4-methoxyphenyl)-2,2-dimethyl-1,3-dioxolan 
• 130796-28-0 (4S,5R)-trans-4--5-(4-methoxyphenyl)-2,2-dimethyl-1,3-dioxolan 
• 130718-67-1 (R)-3-hydroxy-3-(4-methoxyphenyl)-1,1-bis(p-tolylthio)propan-2-one 
• 130718-72-8 threo (2S,3R)-3-(4-methoxyphenyl)-1,1-bis(p-tolylthio)propane-2,3-diol 
• 130718-70-6 erythro (2R,3R)-3-(4-methoxyphenyl)-1,1-bis(p-tolylthio)propane-2,3-diol 
• 130796-38-2 methyl (4R,5R)-cis-5-(4-methoxyphenyl)-2,2-dimethyl-1,3-dioxolan-4-carboxylate 
• 122431-48-5 methyl (4S,5R)-trans-5-(4-methoxyphenyl)-2,2-dimethyl-1,3-dioxolan-4-carboxylate 
• 125073-64-5 (-)-(2R,3R)-methyl-2,3-dihydroxy-3-para-methoxyphenyl-propanoate 
• 122517-80-0 (2S,3R)-(-)-methyl 2,3-dihydroxy-3-(p-methoxyphenyl)propionate 
• 130796-33-7 (4R,5R)-cis-5-(4-methoxyphenyl)-2,2-dimethyl-1,3-dioxolan-4-carboxylic acid 
• 127489-32-1 (4S,5R)-trans-5-(4-methoxyphenyl)-2,2-dimethyl-1,3-dioxolan-4-carboxylic acid 
• 130718-76-2 (4R,5R)-cis-5-(4-methoxyphenyl)-2,2-dimethyl-1,3-dioxolan-4-carbaldehyde 

Relevant articles and documents

Chemoenzymatic Preparation of Enantiomerically Enriched (R)-(–)-Mandelic Acid Derivatives: Application in the Synthesis of the Active Agent Pemoline

The enantioselective resolution of several racemic derivatives of mandelic acid methyl ester catalyzed by lipases from Pseudomonas fluorescens (Amano AK) or Burkholderia cepacia (Amano PS-C II and Amano PS-IM) has been achieved. A gram-scale lipase-mediated kinetic resolution approach has been developed that allows the facile synthesis of the corresponding methyl (R)-(–)-mandelates with excellent enantiomeric excesses (up to >99 % ee) and reaction enantioselectivity (E values up to >200). The dopaminergic agent pemoline, used in the treatment of attention-deficit hyperactivity disorder (ADHD) and narcolepsy, was synthesized with 98 % ee in a straightforward route by condensing the prepared methyl (R)-(–)-mandelate with guanidine hydrochloride under basic conditions. The desired (R)-(+)-pemoline in optically pure form (>99 % ee) was obtained after two recrystallizations from ethanol. However, it was confirmed by chiral HPLC that optically active pemoline undergoes racemization in methanol solution.

Chiral cobalt-catalyzed enantioselective aerobic oxidation of α-hydroxy esters

A chiral cobalt-catalyzed enantioselective aerobic oxidative kinetic resolution of (±)-α-hydroxy esters, using molecular oxygen as a sole oxidant, is reported and a maximum of selectivity factor (s) 31.9 was achieved with >99% enantiomeric excess for unreacted α-hydroxy esters.

Highly enantioselective hydrogenation of α-keto esters catalyzed by Ru-tunephos complexes

Various enantiomerically pure α-hydroxy esters were synthesized by asymmetric hydrogenation of α-keto esters catalyzed by Ru-C n-Tunephos complex. Up to 97.1% ee has been achieved for both α-aryl and α-alkyl substituted α-keto esters. Georg Thieme Verlag Stuttgart.