Binap, (A+-)- → o-Tolylacetic acid

HRID 1088488Notes

Reaction equation

HRID 1088488 reaction equation
[CH2:1]=[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]1[CH2:8][C:9]([OH:11])=[O:10].C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[H][H]>CO>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10]

Participants

5

Reactant 3

HCID 634876Binap, (A+-)-HCID 19424741HCID 19424741, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69519o-Tolylacetic acidYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 100 ml autoclave, the inside atmosphere of which had previously been replaced with argon, were placed 0.3 g (2 mmoles) of 2-methylenephenylacetic acid and 20 ml of methanol. Then, 8.4 mg (0.01 mmole) of Ru((+)-BINAP)(O2CCH3)2 prepared according to the same manner as in Referential Example 3 except using (+)-BINAP in place of (-)-BINAP was added to the mixture to perform hydrogenation for 24 hours at a hydrogen pressure of 100 kg/cm2 and at a reaction temperature of 30° C. to provide 0.3 g of 2-methylphenylacetic acid. The yield was 100%.

Workup

  1. additionwas added to the mixture
  2. customfor 24 hours

Sources & evidence

ORD record
ord-6da473a0536c4507b9f9338a25e9b4e3
Source dataset
uspto-grants-1990_10
Patent number
US04962230

Reaction notes

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