Methanol → Methyl 3-hydroxy-4-methylbenzoate

HRID 1158402Notes

Reaction equation

HRID 1158402 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].OS(O)(=O)=O.[CH3:17]O>>[CH3:17][O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][C:10]([CH3:11])=[C:2]([OH:1])[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 685123-Hydroxy-4-methylbenzoic acid

Product 1

HCID 354091Methyl 3-hydroxy-4-methylbenzoate

Procedure

To a solution of 3-hydroxy-4-methyl-benzoic acid (5 g, 32.8 mmol) in MeOH (100 mL) cc H2SO4 (1 mL) is added. The solution is refluxed for 14 h, then concentrated to about 30 mL and poured into water. The aqueous layer is extracted with ether (50 mL×4) and the combined organic extracts are neutralized with a saturated aqueous solution of NaHCO3 (50 mL×2), washed with brine (50 mL), dried over Na2SO4, filtered and concentrated to give the title compound as a white powder. TLC, Rf (hexane/AcOEt 2:1 )=0.55. 1H-NMR (CDCl3, 300 MHz): δ=2.3 (s, 3H), 3.9 (s, 3H), 7.15 (d, 1H), 7.5 (d, 1H), 7.6 (s, 1H) ppm.

Workup

  1. temperatureThe solution is refluxed for 14 h
  2. concentrationconcentrated to about 30 mL
  3. additionpoured into water
  4. extractionThe aqueous layer is extracted with ether (50 mL×4)
  5. washwashed with brine (50 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-119833760e164ec0bf1de2c1d7368b19
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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