Methanol → Benzoic acid, 2-hydroxy-4-methyl-, methyl ester

HRID 2204672Notes

Reaction equation

HRID 2204672 reaction equation
S(Cl)(Cl)=O.[OH:5][C:6]1[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=[O:9].[CH3:16]O>>[OH:5][C:6]1[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][C:7]=1[C:8]([O:10][CH3:16])=[O:9]

Participants

4

Reactant 3

HCID 887MethanolHCID 57882-Hydroxy-p-toluic acidHCID 24386Thionyl Chloride

Product 1

HCID 78400Benzoic acid, 2-hydroxy-4-methyl-, methyl ester

Conditions

Temperature
50 °C

Procedure

Thionyl chloride (2.16 ml, 29.6 mmol) was added dropwise to a solution of 2-hydroxy-4-methylbenzoic acid (3 g, 19.72 mmol) in methanol (20 ml). The solution was heated at 50° C. for 24 hours. The solution was cooled, the solvent was removed in vacuo and the residue was dissolved in dichloromethane (20 ml), washed with water (15 ml) and saturated NaHCO3 solution (2×10 ml), dried and the solvent removed in vacuo to yield the title compound as an oil. 3.28 g.

Workup

  1. temperatureThe solution was cooled
  2. customthe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in dichloromethane (20 ml)
  4. washwashed with water (15 ml) and saturated NaHCO3 solution (2×10 ml)
  5. customdried
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-08996714a4ac40fe80e3482462fffd24
Source dataset
uspto-grants-2016_06
Patent number
US09365551B2

Reaction notes

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