p-Toluenesulfonic acid → Methyl 4-chloro-3-methoxybenzoate

HRID 2104250Notes

Reaction equation

HRID 2104250 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[O:11][CH3:12].[CH3:13]C1C=CC(S(O)(=O)=O)=CC=1>CO>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:13])=[O:7])=[CH:4][C:3]=1[O:11][CH3:12]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 20633784-Chloro-3-methoxybenzoic acid

Product 1

HCID 44886974Methyl 4-chloro-3-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-chloro-3-methoxybenzoic acid (4.5 g) and 0.5 g of PTSA in 100 mL of dry methanol was refluxed for 3 hours. Evaporation and redissoving in ethyl acetate followed by washing with sodium bicarbonate, and concentration, gave methyl 4-chloro-3-methoxybenzoate without purification.

Workup

  1. customEvaporation
  2. washby washing with sodium bicarbonate, and concentration

Sources & evidence

ORD record
ord-fe794d54465e4a47b94bf40d659d8975
Source dataset
uspto-grants-2009_08
Patent number
US07576218B2

Reaction notes

Loading…