Methanol → HCID 18991986, compound

HRID 375730Notes

Reaction equation

HRID 375730 reaction equation
[OH:1][C:2]1[C:3]([CH3:12])=[C:4]([CH:8]=[C:9]([OH:11])[CH:10]=1)[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[OH-].[Na+].[CH3:20]O>>[OH:1][C:2]1[C:3]([CH3:12])=[C:4]([CH:8]=[C:9]([OH:11])[CH:10]=1)[C:5]([O:7][CH3:20])=[O:6]

Participants

5

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 10953921HCID 10953921, compound

Product 1

HCID 18991986HCID 18991986, compound

Procedure

To 168.2 g of 3,5-dihydroxy-2-methylbenzoic acid in 0.6 l of methanol were added 10 ml of 98% sulfuric acid, and the mixture was heated at reflux for 18 hours. The solution was cooled to room temperature and neutralized by the addition of about 30 ml of 28% sodium hydroxide solution. The solvent was evaporated in vacuo, and the residue was taken up in 0.7 l of ethyl acetate. The solution was washed successively with saturated sodium carbonate solution and brine, dried over sodium sulfate, and the solvent was evaporated in vacuo. The residue was crystallized from ethyl acetate/hexane to yield 162.9 g of methyl 3,5-dihydroxy-2-methylbenzoate, m.p. 136°-138° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 18 hours
  3. customThe solvent was evaporated in vacuo
  4. washThe solution was washed successively with saturated sodium carbonate solution and brine
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was evaporated in vacuo
  7. customThe residue was crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-47607384e7534d6c9211a730287f36c2
Source dataset
uspto-grants-1996_01
Patent number
US05486466

Reaction notes

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