Methanol → Methyl 4-chloro-2-hydroxybenzoate

HRID 904804Notes

Reaction equation

HRID 904804 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([OH:11])[CH:3]=1.[CH3:12]O.S(=O)(=O)(O)O>C1C=CC=CC=1>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:12])=[O:7])=[C:4]([OH:11])[CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 787824-Chlorosalicylic acid

Product 1

HCID 327085Methyl 4-chloro-2-hydroxybenzoate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 4-chloro-2-hydroxybenzoic acid (100 g, 0.58 mol), methanol (500 mL) and concentrated sulfuric acid (50 mL) was refluxed for 20 hr. Benzene (100 mL) was added and the solvent was slowly distilled off from the mixture until 300 mL of distillate was collected. The residue was taken up in diethyl ether, the aqueous phase was separated, the organic phase was washed with sodium bicarbonate solution, dried and evaporated to give 100 g of the title compound as an oil which crystallized on cooling; mp 27°-30° C., and IR (mineral oil) 3150, 1660 and 1600 cm-1.

Workup

  1. distillationthe solvent was slowly distilled off from the mixture until 300 mL of distillate
  2. customwas collected
  3. customthe aqueous phase was separated
  4. washthe organic phase was washed with sodium bicarbonate solution
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-a8577e33de53401eb4af5d1c795fe71b
Source dataset
uspto-grants-1983_12
Patent number
US04420476

Reaction notes

Loading…