117195-36-5

Basic information

• Product Name: Benzeneacetic acid, a-butyl-a-hydroxy-, (R)-
• CAS NO: 117195-36-5
• Molecular Formula: C12H16O3
• Molecular Weight: 208.257
• Mol File: 117195-36-5.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: Benzeneacetic acid, a-butyl-a-hydroxy-, (R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzeneacetic acid, a-butyl-a-hydroxy-, (R)-(117195-36-5)
• EPA Substance Registry System: Benzeneacetic acid, a-butyl-a-hydroxy-, (R)-(117195-36-5)

Safety Data

• Hazardous Substances Data: 117195-36-5(Hazardous Substances Data)

Upstream product

• 136032-07-0 (-)-<(1R,2S)-2-phenylcyclohex-1-yl>phenylglyoxalate 
• 20229-41-8 l-menthyl phenylglyoxylate 
• 611-73-4 Benzoylformic acid 
• 141652-48-4 <(1R,2R)-2-phenoxycyclohex-1-yl> phenylglyoxalate 
• 177981-47-4 (1R,2R)-2-nitroxycyclohexyl phenylglyoxylate 
• 42930-39-2 n-butylzinc chloride 
• 173031-14-6 <(1R,2R)-2-(4-phenylphenoxy)cyclohexan-1-yl> phenylglyoxylate 
• 173031-08-8 <(1R,2R)-2-(4-tert-butylphenoxy)cyclohexan-1-yl> phenylglyoxylate 
• 71065-25-3 phenyl-2 hydroxy-2 hexanoate de (-) menthyle 
• 71065-25-3 2-Hydroxy-2-phenyl-hexanoic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 136158-42-4 (R)-1-Phenyl-1-((2S,3S)-3-trimethylsilanyl-oxiranyl)-pentan-1-ol 
• 137024-41-0 (S)-3-Phenyl-hept-1-en-3-ol 
• 1074-12-0 phenylglyoxal hydrate 

Relevant articles and documents

trans-2-phenoxycyclohexan-1-ol as new chiral auxiliary: Synthesis of chiral α-hydroxy acids

(1R,2R)-2-phenoxycyclohexan-1-ol is used as a chiral auxiliary for the preparation of α-hydroxy acids in high optical purities.

Isomannide and isosorbide as new chiral auxiliaries for the stereoselective synthesis of tertiary α-hydroxy acids

Isomannide and isosorbide are selectively protected to provide new chiral auxiliaries suitable for the preparation of enantiopure tertiary α-hydroxy acids. Diastereoselective additions of organozinc reagents on the derived phenylglyoxylates afford the desired α-hydroxy acids with 60-99% ee after saponification. Both absolute configurations of the α-hydroxy acids can be accessed, by adapted choice of either the starting diol or the protecting group.

New cyclohexyl-based chiral auxiliaries: Enantioselective synthesis of α-hydroxy acids

(1R,2R)-2-(4-tert-butylphenoxy) cyclohexan-1-ol (5) and (1R,2R)-2-(4-phenylphenoxy) cyclohexan-1-ol (6) have been used for the first time as chiral auxiliaries. Addition of alkylzinc chlorides to the corresponding glyoxylates 5a, 6a, after hydrolysis, provided (R)-α-hydroxy acids in high optical purities.