Water → [2-(3-Hydroxypropyl)phenyl]acetic acid

HRID 46991Notes

Reaction equation

HRID 46991 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][C:12]#N.[OH-:14].[Na+].[OH2:16]>C(O)C>[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][C:12]([OH:16])=[O:14]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 22645929[2-(3-Hydroxypropyl)phenyl]acetonitrile

Product 1

HCID 20386052[2-(3-Hydroxypropyl)phenyl]acetic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of [2-(3-hydroxypropyl)phenyl]acetonitrile (52.5 g., 0.30 mole) and sodium hydroxide (40 g., 1.0 mole) in water (200 ml.) and ethanol (600 ml.) is heated at reflux for 18 hours. The solution is concentrated in vacuo to about half-volume. Water (600 ml.) is added and the resulting solution is acidified with 6 N hydrochloric acid. The precipitated product acid is taken up in ether, washed with water, and dried over magnesium sulfate. The ether is evaporated in vacuo to afford [2-(3-hydroxypropyl)phenyl]acetic acid.

Workup

  1. temperatureat reflux for 18 hours
  2. concentrationThe solution is concentrated in vacuo to about half-volume
  3. additionWater (600 ml.) is added
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. customThe ether is evaporated in vacuo

Sources & evidence

ORD record
ord-8c9af75524ad440a9b8550e0f9c53c25
Source dataset
uspto-grants-1979_11
Patent number
US04175203

Reaction notes

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