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

HRID 26624Notes

Reaction equation

HRID 26624 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-03668b75de1f4066b26381ad6a5b7f3a
Source dataset
uspto-grants-1979_04
Patent number
US04150235

Reaction notes

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