Methanol → Methyl 3-chloro-4-hydroxybenzoate

HRID 1283639Notes

Reaction equation

HRID 1283639 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH3:17]O>>[CH3:17][O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][C:10]([OH:11])=[C:2]([Cl:1])[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 198603-Chloro-4-hydroxybenzoic acid

Product 1

HCID 77580Methyl 3-chloro-4-hydroxybenzoate

Procedure

A solution of 25 g. (0.14 mol.) of 3-chloro-4-hydroxybenzoic acid in 200 ml. of methanol containing 2 ml. of sulfuric acid was refluxed for 12 hours. After cooling, excess methanol was evaporated, water was added to the residue and it was made basic with 10% aqueous sodium hydroxide. The precipitate was collected, washed with water and dried in vacuo to give 3-chloro-4-hydroxybenzoic acid methyl ester, m.p. 105°-107°C.

Workup

  1. temperatureAfter cooling
  2. customexcess methanol was evaporated
  3. additionwater was added to the residue and it
  4. customThe precipitate was collected
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-92643912fc1f473d8b106a31004ef742
Source dataset
uspto-grants-1976_08
Patent number
US03975537

Reaction notes

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