Methanol → Methyl 3-hydroxy-2-methylbenzoate

HRID 577546Notes

Reaction equation

HRID 577546 reaction equation
[OH:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].S(Cl)(Cl)=O.[CH3:16]O>>[OH:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH3:16])=[O:6]

Participants

4

Reactant 3

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

Product 1

HCID 12488879Methyl 3-hydroxy-2-methylbenzoateYield 84%

Procedure

To a solution of 3-hydroxy-2-methylbenzoic acid (3.80 g, 25.0 mmol) in methanol (3.0 mL) at 0° C. was added thionyl chloride (3.00 mL, 41.2 mmol) dropwise. The reaction was allowed to warm to room temperature and was then heated at 50° C. for 2 hours. The solvent was removed under vacuum and the resulting solids were dissolved in ethyl acetate and washed with NaHCO3 (sat. aq.). The ethyl acetate layer was dried over Na2SO4, filtered, and concentrated under vacuum to give methyl 3-hydroxy-2-methylbenzoate (114a, 3.49 g, 84% yield) as a light tan solid.

Workup

  1. temperaturewas then heated at 50° C. for 2 hours
  2. customThe solvent was removed under vacuum
  3. dissolutionthe resulting solids were dissolved in ethyl acetate
  4. washwashed with NaHCO3 (sat. aq.)
  5. dry with materialThe ethyl acetate layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-0f308d5d2d114f28944a413dffe5c888
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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