Binap, (A+-)- → (2R)-2-(4-methoxyphenyl)propanoic acid

HRID 1088495Notes

Reaction equation

HRID 1088495 reaction equation
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]([C:7](=[CH2:11])[C:8]([OH:10])=[O:9])=[CH:5][CH:4]=1.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][O:2][C:3]1[CH:4]=[CH:5][C:6]([C@@H:7]([CH3:11])[C:8]([OH:10])=[O:9])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 634876Binap, (A+-)-HCID 145737872-(4-Methoxyphenyl)prop-2-enoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 12398858(2R)-2-(4-methoxyphenyl)propanoic acidYield 89%

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 0.36 g (2 mmoles) of p-methoxyatropic acid and 20 ml of methanol. Then, 7.5 mg (0.009 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 12 hours at a hydrogen pressure of 100 kg/cm2 and at a reaction temperature of 19° C. Thereafter, the solvent was distilled off to provide 0.32 g of (2R)-(-)-2-(p-methoxyphenyl)propionic acid. The yield was 89%.

Workup

  1. additionwas added to the mixture
  2. customfor 12 hours
  3. customat a reaction temperature of 19° C
  4. distillationThereafter, the solvent was distilled off

Sources & evidence

ORD record
ord-e6078a986a80410fbca8c058ab4aca0c
Source dataset
uspto-grants-1990_10
Patent number
US04962230

Reaction notes

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