Hydrochloric Acid → Methyl 5-chloro-3-formyl-2-hydroxybenzoate

HRID 1761903Notes

Reaction equation

HRID 1761903 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[O:13])[C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].Cl.S(Cl)(Cl)=O.[CH3:19]O>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[O:13])[C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([O:9][CH3:19])=[O:8]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 24386Thionyl ChlorideHCID 1833565-Chloro-3-formyl-2-hydroxybenzoic acid

Product 1

HCID 13146779Methyl 5-chloro-3-formyl-2-hydroxybenzoate

Procedure

193 g of 5-chloro-3-formyl-2-hydroxybenzoic acid are dissoved in 2 liters of methanol and the solution is saturated with hydrogen chloride. 100 ml of thionyl chloride are added to the solution and the mixture is refluxed for 8 hours. After cooling, the resultant crystals are collected by filtration and dried to give 190 g of methyl 5-chloro-3-formyl-2-hydroxybenzoate.

Workup

  1. temperaturethe mixture is refluxed for 8 hours
  2. temperatureAfter cooling
  3. filtrationthe resultant crystals are collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-1e56515e547646cc800282f9f8fb4e31
Source dataset
uspto-grants-1989_05
Patent number
US04829067

Reaction notes

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