Methanol → Methyl 3-hydroxy-2-methylbenzoate

HRID 906086Notes

Reaction equation

HRID 906086 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(=O)(=O)(O)O.[CH3:17]O>>[OH:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH3:17])=[O:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 2520233-Hydroxy-2-methylbenzoic Acid

Product 1

HCID 12488879Methyl 3-hydroxy-2-methylbenzoateYield 100%

Procedure

A solution of 3-hydroxy-2-methylbenzoic acid (5 g, 33 mmol) and sulfuric acid (500 μl) in methanol (20 mL) was stirred at reflux for 15 hours. The reaction mixture was allowed to cool to room temperature and partitioned between water and ethyl acetate. The aqueous portion was extracted with ethyl acetate and the combined organic portion was washed with saturated sodium bicarbonate, brine, and then was dried over sodium sulfate, filtered and concentrated under reduced pressure to afford (5.46 g, 100%) of methyl 3-hydroxy-2-methylbenzoate. 1H NMR (400 MHz, DMSO-d6): 9.71 (s, 1H), 7.20-7.17 (m, 1H), 7.11-7.07 (m, 1H), 7.01-6.97 (m, 1H), 3.79 (s, 3H), 2.28 (s, 3H). MS (EI) for C9H10O3: 166 (MH+).

Workup

  1. temperatureat reflux for 15 hours
  2. custompartitioned between water and ethyl acetate
  3. extractionThe aqueous portion was extracted with ethyl acetate
  4. washthe combined organic portion was washed with saturated sodium bicarbonate, brine
  5. dry with materialwas dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f885839ca5a64d3da62a526571a7fb02
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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