Water → 2-Methoxy-6-methylbenzoic acid

HRID 582371

Reaction equation

HRID 582371 reaction equation
[CH3:1][C:2]1[C:7]([C:8]([O:10]CC)=[O:9])=[C:6]([O:13][CH3:14])[CH:5]=[CH:4][CH:3]=1.O.[OH-].[Na+]>C(O)C>[CH3:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[C:6]([O:13][CH3:14])[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 5910602-Methoxy-6-methyl-benzoic acid ethyl ester

Product 1

HCID 2731702-Methoxy-6-methylbenzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 6-methyl-2-methoxybenzoate (642.0 g, 3.3 mol), water (2.5 l), ethanol (4.0 l) and sodium hydroxide (270 g, 6.6 mol) is heated under reflux with stirring for 20 hours. Subsequently, ethanol is distilled off and the reaction mixture is diluted with water, acidified with concentrated hydrochloric acid. The solid material is collected by vacuum filtration, washed with water and dried yielding off-white crystals, 460.0 g (83.9%).

Workup

  1. temperatureis heated
  2. temperatureunder reflux
  3. distillationSubsequently, ethanol is distilled off
  4. additionthe reaction mixture is diluted with water
  5. filtrationThe solid material is collected by vacuum filtration
  6. washwashed with water
  7. customdried
  8. customyielding off-white crystals, 460.0 g (83.9%)

Sources & evidence

ORD record
ord-07b0bba962794763b65a87b7bc7fd58d
Source dataset
uspto-grants-1999_07
Patent number
US05922905

Linked notes

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