Methanol → Methyl 3,5-Dihydroxybenzoate

HRID 709671Notes

Reaction equation

HRID 709671 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([OH:11])[CH:10]=1)[C:5]([OH:7])=[O:6].S(Cl)(Cl)=O.[CH3:16]O>>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([OH:11])[CH:10]=1)[C:5]([O:7][CH3:16])=[O:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 74243,5-Dihydroxybenzoic AcidHCID 24386Thionyl Chloride

Product 1

HCID 75076Methyl 3,5-Dihydroxybenzoate

Procedure

To a solution of 3,5-dihydroxybenzoic acid (30.0 g) in methanol (300 mL) was added dropwise thionyl chloride (20 mL) at 0° C., and the mixture was heated under reflux for 2 hr. The reaction mixture was concentrated, and the obtained crystals were washed with diethyl ether to give the title compound (30.0 g) as a white solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hr
  3. concentrationThe reaction mixture was concentrated
  4. washthe obtained crystals were washed with diethyl ether

Sources & evidence

ORD record
ord-6430e51fafa84f3c8ce622c229c772ab
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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