Methanol → Methyl 4-formyl-3-hydroxybenzoate

HRID 1498089Notes

Reaction equation

HRID 1498089 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[OH:12])=[O:2].S(Cl)(Cl)=O.[CH3:17]O>>[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([O:9][CH3:17])=[O:8])=[CH:5][C:4]=1[OH:12])=[O:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 3175084-Formyl-3-hydroxybenzoic acid

Product 1

HCID 14395860Methyl 4-formyl-3-hydroxybenzoateYield 85%

Procedure

4-Formyl-3-hydroxybenzoic acid (5 g, 30 mmol) was suspended in methanol (70 mL), and treated with thionyl chloride (3.29 mL 45 mmol) dropwise. The mixture was heated to reflux overnight. Concentrated to dryness, and 50 mL of toluene was added, and concentrated again. The residue was recrystallized from ethyl acetate-hexane. A total of 4.8 g (85%) of methyl 4-formyl-3-hydroxybenzoate was obtained.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. concentrationConcentrated to dryness, and 50 mL of toluene
  4. additionwas added
  5. concentrationconcentrated again
  6. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-34eccad21147493dbb120a9b8502b127
Source dataset
uspto-grants-2015_12
Patent number
US09198918B2

Reaction notes

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