Methanol → Methyl 4-formyl-3-hydroxybenzoate

HRID 1530410Notes

Reaction equation

HRID 1530410 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-0cced4af82244bd68f16bb07ebd8097d
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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