Benzoic Acid → Methyl 3-Hydroxybenzoate

HRID 725705Notes

Reaction equation

HRID 725705 reaction equation
Cl.[C:2]([O:5][CH2:6]C)(=[O:4])[CH3:3].[CH3:8][CH2:9][CH2:10][CH2:11][CH2:12]C.C(O)(=[O:21])C1C=CC=CC=1>CO>[OH:21][C:9]1[CH:8]=[C:3]([CH:12]=[CH:11][CH:10]=1)[C:2]([O:5][CH3:6])=[O:4]

Participants

5

Reactant 3

HCID 243Benzoic AcidHCID 313Hydrochloric AcidHCID 21226206Ethyl acetate hexane

Product 1

HCID 88068Methyl 3-HydroxybenzoateYield 61%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

m-Hydroxybenzoic acid (10 g, 72.5 mmol) was dissolved in 100 mL of methanol and the solution refluxed with a catalytic amount of HCl. After 24 hours tlc analysis on silica with 10% ethyl acetate/hexane revealed a trace of the starting benzoic acid remaining. The solution was cooled and concentrated to dryness. The solid residue was dissolved in 200 mL of ether and washed with 100 mL of saturated aq. NaHCO3 and brine. Drying the solution over MgSO4 and evaporating the solvent left a slightly yellow solid that was purified by recrystallization from benzene/cyclohexane to give methyl 3-hydroxybenzoate as a white solid (6.74 g, 61%): 71°-73° C. ##STR43##

Workup

  1. temperatureThe solution was cooled
  2. concentrationconcentrated to dryness
  3. dissolutionThe solid residue was dissolved in 200 mL of ether
  4. washwashed with 100 mL of saturated aq. NaHCO3 and brine
  5. dry with materialDrying the solution over MgSO4
  6. customevaporating the solvent
  7. waitleft a slightly yellow solid
  8. customthat was purified by recrystallization from benzene/cyclohexane

Sources & evidence

ORD record
ord-dfe4fbc1ba674ee7959f0764e99f8009
Source dataset
uspto-grants-1998_01
Patent number
US05707559

Reaction notes

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