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

HRID 864378Notes

Reaction equation

HRID 864378 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×). 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×)
  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-188a3388684b495493cafa111d6963d0
Source dataset
uspto-grants-1996_10
Patent number
US05563142

Reaction notes

Loading…