2-Phenylpropionic acid → Methyl alpha-methylbenzeneacetate

HRID 2203302Notes

Reaction equation

HRID 2203302 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[C:8]1([CH:14]([CH3:18])[C:15]([OH:17])=[O:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1C=CC=CC=1.CO>[C:8]1([CH:14]([CH3:18])[C:15]([O:17][CH3:1])=[O:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 102962-Phenylpropionic acidHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 569653Methyl alpha-methylbenzeneacetate

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 887MethanolSolvent

Procedure

Trimethylsilyl diazomethane (2.0M in hexanes, 40 mL, 80 mmol) was added dropwise to a solution of racemic 2-phenylpropionic acid (10.0 g, 66.6 mmol) in benzene (100 mL) and methanol (20 mL) cooled in an ice bath. After the addition was complete the reaction solution was stirred at room temperature for 2 hours. The solution was then concentrated to give the indicated product. m/z=165.1 (M+H).

Workup

  1. temperaturecooled in an ice bath
  2. additionAfter the addition
  3. concentrationThe solution was then concentrated
  4. customto give the indicated product

Sources & evidence

ORD record
ord-25442001945043bd9b6a5b6db5be979c
Source dataset
uspto-grants-2016_06
Patent number
US09365574B2

Reaction notes

Loading…