Hydrochloric Acid → Benzoic acid, 2-hydroxy-4-methyl-, methyl ester

HRID 37010Notes

Reaction equation

HRID 37010 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=[O:7].Cl.[CH3:13]O>>[CH3:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5](=[CH:9][CH:10]=1)[C:6]([O:8][CH3:13])=[O:7]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 57882-Hydroxy-p-toluic acid

Product 1

HCID 78400Benzoic acid, 2-hydroxy-4-methyl-, methyl esterYield 94%

Conditions

Temperature
60 °C

Procedure

To a suspension of 10 g (0.0651 mol) of 4-methylsalicylic acid in 150 mL of methanol was added 50 mL of ethereal hydrochloric acid. The reaction mixture was heated at 60° C. for 60 hours. The solvent was removed under vacuum. After adding hexane-ethyl acetate, the resulting solid was filtered and the filtrate was evaporated to give 10.2 g (94%) of product as an oil.

Workup

  1. customThe solvent was removed under vacuum
  2. additionAfter adding hexane-ethyl acetate
  3. filtrationthe resulting solid was filtered
  4. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-6b6d9b4baeee4fe68ec10f9a0f3c0772
Source dataset
uspto-grants-1995_05
Patent number
US05418250

Reaction notes

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