Methane → 2-Methoxy-3,5-dimethylbenzoic acid

HRID 1288274Notes

Reaction equation

HRID 1288274 reaction equation
[Na][Na].[OH:3][C:4]1[C:12]([CH3:13])=[CH:11][C:10]([CH3:14])=[CH:9][C:5]=1[C:6]([OH:8])=[O:7].S(OC)(O[CH3:19])(=O)=O.[OH-].[Na+].C>O>[CH3:19][O:3][C:4]1[C:12]([CH3:13])=[CH:11][C:10]([CH3:14])=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]

Participants

7

Reactant 5

HCID 297MethaneHCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 803903,5-Dimethylsalicylic acidHCID 141233Disodium

Product 1

HCID 189546082-Methoxy-3,5-dimethylbenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

The disodium salt of 2-hydroxy-3,5-dimethylbenzoic acid (21 g.) and dimethyl sulphate (92 ml.) were stirred together at 140°-150° C. for 2.5 hours. After standing overnight, the mixture was added to a solution of sodium hydroxide (40 g.) in water (250 ml.), and the mixture stirred and heated on the steam-bath for 1 hour. Charcoal was added, the mixture was filtered and the filtrate was cooled, acidified with concentrated hydrochloric acid, and maintained at 0° C. The solid which separated was filtered off and recrystallised from aqueous ethanol to give 2-methoxy-3,5-dimethylbenzoic acid (14.7 g.), m.p. 97°-98° C.

Workup

  1. temperatureheated on the steam-bath for 1 hour
  2. filtrationthe mixture was filtered
  3. temperaturethe filtrate was cooled
  4. customThe solid which separated
  5. filtrationwas filtered off
  6. customrecrystallised from aqueous ethanol

Sources & evidence

ORD record
ord-eff5481aa2bf4369935108dde9d25c6c
Source dataset
uspto-grants-1976_10
Patent number
US03987160

Reaction notes

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