Methanol → Methyl 4-ethyl-3-hydroxybenzoate

HRID 1158443Notes

Reaction equation

HRID 1158443 reaction equation
[CH2:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[OH:12])[CH3:2].[CH3:13]O>OS(O)(=O)=O>[CH3:13][O:8][C:7](=[O:9])[C:6]1[CH:10]=[CH:11][C:3]([CH2:1][CH3:2])=[C:4]([OH:12])[CH:5]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 215064424-Ethyl-3-hydroxybenzoic acid

Product 1

HCID 54428408Methyl 4-ethyl-3-hydroxybenzoate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 4-ethyl-3-hydroxy-benzoic acid (3.76 g, 22.6 mmol) in MeOH (70 mL), cc H2SO4 (0.7 mL) is added. The solution is refluxed overnight, 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 (CH2Cl2/MeOH 95:5)=0.7, MS (LC-MS): 179.2 [M−H]−, tR (HPLC, Nucleosil C18 column, 10-100% CH3CN/H2O/5 min, 100% CH3CN/2.8 min, flow: 1 ml/min): 4.86 min.

Workup

  1. temperatureThe solution is refluxed overnight
  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-c79f931c4fe949a8bb944cd4882a6246
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

Loading…