Hydrochloric Acid → Methyl Gentisate

HRID 2292308Notes

Reaction equation

HRID 2292308 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl.[CH3:13]O>>[CH3:13][O:5][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([OH:11])[CH:9]=[CH:10][C:2]=1[OH:1]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 34692,5-Dihydroxybenzoic acid

Product 1

HCID 75077Methyl Gentisate

Procedure

2,5-Dihydroxybenzoic acid (30 g) was added to methanol (100 ml) which had been acidified with hydrogen chloride gas. The solution was refluxed for 12 hours when the solvent was removed. The resulting solid was taken up in diethyl ether (200 ml) and washed with water (2×100 ml). The organic layer was dried over magnesium sulphate and the solvent removed under vacuum. The resulting solid (30 g) (m.p. 83°-84° C.) was identified as the desired methyl ester.

Workup

  1. temperatureThe solution was refluxed for 12 hours when the solvent
  2. customwas removed
  3. washwashed with water (2×100 ml)
  4. dry with materialThe organic layer was dried over magnesium sulphate
  5. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-3fd6b63a61f14d2486763fe56776a756
Source dataset
uspto-grants-1989_01
Patent number
US04801735

Reaction notes

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