Ethanol → 2-(3-Bromo-5-methoxyphenyl)acetic acid

HRID 542739Notes

Reaction equation

HRID 542739 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:11][CH3:12])[CH:5]=[C:6](CC#N)[CH:7]=1.[OH-:13].[Na+].[CH2:15]([OH:17])[CH3:16]>>[Br:1][C:2]1[CH:3]=[C:4]([O:11][CH3:12])[CH:5]=[C:6]([CH2:16][C:15]([OH:13])=[O:17])[CH:7]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 212429652-(3-Bromo-5-methoxyphenyl)acetonitrile

Product 1

HCID 212429042-(3-Bromo-5-methoxyphenyl)acetic acid

Procedure

A mixture of 5-bromo-3-methoxyphenylacetonitrile (22.6 g, 0.1 m) and 10% aqueous sodium hydroxide (300 ml) in ethanol (225 ml) is heated to 95° for 18 hours. The mixture is concentrated in vacuo, acidified with 10% hydrochloric acid and extracted with ethyl acetate. The ethyl acetate extract is washed, dried with sodium sulfate and concentrated in vacuo to give 5-bromo-3-methoxyphenylacetic acid.

Workup

  1. temperatureis heated to 95° for 18 hours
  2. concentrationThe mixture is concentrated in vacuo
  3. extractionextracted with ethyl acetate
  4. extractionThe ethyl acetate extract
  5. washis washed
  6. dry with materialdried with sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-806a1132f0874682accb093aca335200
Source dataset
uspto-grants-1987_04
Patent number
US04659706

Reaction notes

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