Ethanol → HCID 14519886, compound

HRID 1198628Notes

Reaction equation

HRID 1198628 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5](CC#N)=[C:4]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:3]=1.[OH-:19].[Na+].[CH2:21]([OH:23])[CH3:22]>O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:22][C:21]([OH:19])=[O:23])=[C:4]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 14519885HCID 14519885, compound

Product 1

HCID 14519886HCID 14519886, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. customthe ethanol was removed under vacuum
  4. additionThe residue was diluted with water
  5. washwashed with benzene
  6. customto give an oil which
  7. extractionwas extracted into ethyl acetate

Sources & evidence

ORD record
ord-69c060e018764a4eb5982fbd5a4a64b8
Source dataset
uspto-grants-1994_01
Patent number
US05281620

Reaction notes

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