Methanol → Methyl 3-hydroxy-2-methylbenzoate

HRID 1017591Notes

Reaction equation

HRID 1017591 reaction equation
S(Cl)(Cl)=O.[OH:5][C:6]1[C:7]([CH3:15])=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([OH:11])=[O:10].[CH3:16]O>>[OH:5][C:6]1[C:7]([CH3:15])=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([O:11][CH3:16])=[O:10]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 2520233-Hydroxy-2-methylbenzoic Acid

Product 1

HCID 12488879Methyl 3-hydroxy-2-methylbenzoate

Procedure

To a methanol solution (25 mL) at 0° C. was dropwise added thionyl chloride (9.6 mL, 0.13 mol). After 15 minutes, 3-hydroxy-2-methylbenzoic acid (4 g, 0.033 mol) was added and the resulting mixture was stirred at room temperature for 24 hours. Volatile was removed under vacuo and the residue was partitioned between water and ethyl acetate. The organic layer was separated, washed with water and saturated sodium chloride solution, and was dried over sodium sulfate. After concentration, the crude product was recrystallized from dichloromethane and hexane to gave 3.48 g of methyl 3-hydroxy-2-methylbenzoate.

Workup

  1. customat 0° C.
  2. customVolatile was removed under vacuo
  3. customthe residue was partitioned between water and ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with water and saturated sodium chloride solution
  6. dry with materialwas dried over sodium sulfate
  7. concentrationAfter concentration
  8. customthe crude product was recrystallized from dichloromethane and hexane

Sources & evidence

ORD record
ord-7f170147151e4dc0b5f18f9a63ac87c3
Source dataset
uspto-grants-2002_11
Patent number
US06479490B2

Reaction notes

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