Methyl Salicylate → Benzoic acid, 5-chloro-2-hydroxy-, methyl ester

HRID 979982Notes

Reaction equation

HRID 979982 reaction equation
[Cl:1]Cl.[C:3]([O:12][CH3:13])(=[O:11])[C:4]1[C:5](=[CH:7][CH:8]=[CH:9][CH:10]=1)[OH:6]>C(Cl)(Cl)Cl>[Cl:1][C:9]1[CH:10]=[C:4]([C:3]([O:12][CH3:13])=[O:11])[C:5]([OH:6])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 4133Methyl SalicylateHCID 24526Chlorine

Product 1

HCID 77684Benzoic acid, 5-chloro-2-hydroxy-, methyl ester

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A 85.2 g quantity of chlorine gas was absorbed in a mixture of 152 g (1.0 mole) of methyl salicylate and 500 ml of chloroform at less than 20° C. over a period of 6 hours while the mixture was stirred. The resulting reaction mixture was washed with water and the chloroform was removed. The residue was subjected to fractional distillation at reduced pressure to provide 152 g (81.5%) of a fraction at 117° to 120° C. and 8 mmHg., M.P. 51° C.

Workup

  1. customThe resulting reaction mixture
  2. washwas washed with water
  3. customthe chloroform was removed
  4. distillationThe residue was subjected to fractional distillation at reduced pressure
  5. customto provide 152 g (81.5%) of a fraction at 117° to 120° C.

Sources & evidence

ORD record
ord-ca0c90f4aadd42c8b671ba0080c61626
Source dataset
uspto-grants-1987_01
Patent number
US04634768

Reaction notes

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