HCID 14519886, compound → HCID 14519887, compound

HRID 1198629Notes

Reaction equation

HRID 1198629 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[C:4]([O:12]CC2C=CC=CC=2)[CH:3]=1>C(O)C.[Pd]>[OH:12][C:4]1[CH:3]=[C:2]([CH3:1])[CH:7]=[CH:6][C:5]=1[CH2:8][C:9]([OH:11])=[O:10]

Participants

4

Reactant 1

HCID 14519886HCID 14519886, compound

Product 1

HCID 14519887HCID 14519887, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of crude 2-(4-methyl-2-phenylmethoxyphenyl)acetonitrile (15 g, 63 mmol) in ethanol (200 ml) and water (50 ml) containing 10 g (0.25 mol) NaOH was heated under reflux overnight, and the ethanol was removed under vacuum. The residue was diluted with water and washed with benzene. The aqueous layer was then acidified with dilute HCl to give an oil which was extracted into ethyl acetate to give (4-methyl-2-phenylmethoxyphenyl)acetic acid (14.2 g, 88%) as an oil which solidified on standing. A solution of this crude (4-methyl-2-phenylmethoxyphenyl)acetic acid in ethanol was hydrogenated over palladium on charcoal to give (2-hydroxy-4-methylphenyl)acetic acid. Anal (C9H10O3) C,H.

Sources & evidence

ORD record
ord-c8eb050728ad4917ba80d15c2f51a585
Source dataset
uspto-grants-1994_01
Patent number
US05281620

Reaction notes

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