Binap, (A+-)- → 3-Phenylbutyric acid

HRID 1088494Notes

Reaction equation

HRID 1088494 reaction equation
C[C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)/[CH:5]=[CH:6]\[C:7]([OH:9])=[O:8].[CH:13]1C=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>[C:4]1([CH:5]([CH3:13])[CH2:6][C:7]([OH:9])=[O:8])[CH:3]=[CH:2][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 634876Binap, (A+-)-HCID 2529400(2Z)-3-(3-Methylphenyl)-2-propenoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 207243-Phenylbutyric 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 0.32 g (2 mmoles) of (Z)-3-methylcinnamic acid and 20 ml of methanol. Then, 2.9 mg (0.0034 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 70 hours at a hydrogen pressure of 104 kg/cm2 and at a reaction temperature of 25° C. Thereafter, the solvent was distilled off to provide 0.32 g of 3-phenylbutyric acid. The yield was 100%.

Workup

  1. additionwas added to the mixture
  2. customfor 70 hours
  3. customat a reaction temperature of 25° C
  4. distillationThereafter, the solvent was distilled off

Sources & evidence

ORD record
ord-1f6d0cd8c9c146658d7e487e6671b2e3
Source dataset
uspto-grants-1990_10
Patent number
US04962230

Reaction notes

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