135366-65-3

Basic information

• Product Name: methyl β-hydroxy-α-phenylvalerate
• Synonyms: methyl β-hydroxy-α-phenylvalerate
• CAS NO: 135366-65-3
• Molecular Weight: 208.257
• Mol File: 135366-65-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: methyl β-hydroxy-α-phenylvalerate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl β-hydroxy-α-phenylvalerate(135366-65-3)
• EPA Substance Registry System: methyl β-hydroxy-α-phenylvalerate(135366-65-3)

Safety Data

• Hazardous Substances Data: 135366-65-3(Hazardous Substances Data)

Upstream product

• 67-64-1 acetone 
• 101-41-7 benzeneacetic acid methyl ester 
• 4358-87-6 (RS)-methyl mandelate 
• 74087-85-7 3,3-dimethyldioxirane 
• 22979-35-7 Methyl phenyldiazoacetate 
• 67-63-0 isopropyl alcohol 
• 186581-53-3 diazomethane 
• 6343-61-9 3-Hydroxy-3-methyl-2-phenylbutanoic acid 

Relevant articles and documents

Dimethyldioxirane Oxidation of Titanium Enolates: Diastereoselective α-Hydroxylations

The oxidation of titanium enolates, derived from a transmetalation of the corresponding lithium enolates with (i-PrO)3TiCl, (Et2N)3TiCl, or Cp2TiCl2, by dimethyldioxirane has been investigated.Furthermore, the diastereoselective hydroxylation of the chiral metal enolates, e.g., derived from camphor (1f), menthone (1g), flavanone (1h), and 2-benzylcyclopentanone (1i), by dimethyldioxirane has been examined.The diastereoselectivity of the oxygen transfer strongly depends on the metal partner coordinated to the enolate.The titanium enolates 4 resulted in much higher diastereoselectivities (up to 96percent de) than the corresponding sodium enolates 5 and at least as high if not higher than the silyl enol ethers 6.Moreover, the aldol reaction of ester-derived sodium enolates with acetone, the unavoidable medium for dimethyldioxirane, could be totally suppressed by the use of the chlorotitanocene enolates 4.Thus, the oxidation of chiral titanium enolates by dimethyldioxirane represents a general, convenient, effective, and chemo- and diastereoselective synthesis of α-hydroxy carbonyl compounds.

Highly Efficient Hydroxylation of Carbonyl Compounds with Dimethyldioxirane

The enolates and/or enols of ketones, esters, β-diketones, β-oxo esters, and β-oxolactones were transformed by dimethyldioxirane (isolated in acetone solution or generated in situ) into their α-hydroxy compounds in good to excellent yields.The direct hydroxylation of the enols was significantly enhanced by the use of fluoride ion.For the enolate of camphor the exo/endo diastereoselectivity depended significantly on the metal ligand; the highest exo/endo ratio (93:7) was observed for the enol trimethylsilyl ether of camphor.Key Words: Dimethyldioxirane / Enolates / Hydroxylation / α-Hydroxy carbonyl compounds / Enol silyl ethers

Unambiguous Proof for Alcoxycarbonyl-group Migration in Wagner-Meerwein Rearrangements

In HSO3F/SO2ClF the β-hydroxy esters Ph-CHOH-CMe2-COOR (1, R=Me, Et) are doubly protonated, then transformed into the fluorosulfates 7 and (partly) into the fluorides 8.At -15 deg C, both 7 and 8 undergo a rearrangement, forming derivatives of Me2C=C(Ph)C