Hydrochloric Acid → 3,5-Dimethyl-p-anisic acid

HRID 2395732Notes

Reaction equation

HRID 2395732 reaction equation
C([O:3][C:4](=[O:15])[C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([O:12][CH3:13])=[C:7]([CH3:14])[CH:6]=1)C.Cl>[OH-].[Na+]>[CH3:14][C:7]1[CH:6]=[C:5]([CH:10]=[C:9]([CH3:11])[C:8]=1[O:12][CH3:13])[C:4]([OH:15])=[O:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 53404664Ethyl 4-methoxy-3,5-dimethylbenzoate

Product 1

HCID 889443,5-Dimethyl-p-anisic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 3,5-dimethyl-4-methoxybenzoic acid ethyl ester (PREPARATION 2, 10.5 g) and aqueous sodium hydroxide (20%, 100 ml) is refluxed for 18 hours. The solution is cooled and acidified with hydrochloric acid (12N, pH 2). The acidified solution is extracted with chloroform (3 X). The combined extracts are dried over sodium sulfate and concentrated under reduced pressure to give a solid which is recrystallized from ether/pet ether mixture to give the title compound, mp 189°-191°.

Workup

  1. temperatureis refluxed for 18 hours
  2. temperatureThe solution is cooled
  3. extractionThe acidified solution is extracted with chloroform (3 X)
  4. dry with materialThe combined extracts are dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give a solid which
  7. customis recrystallized from ether/pet ether mixture

Sources & evidence

ORD record
ord-fd6558e349bb4843a460cc185f6c6402
Source dataset
uspto-grants-1996_02
Patent number
US05489593

Reaction notes

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