5-Chlorosalicylic Acid → 5-Chloro-2-hydroxybenzoyl chloride

HRID 457938

Reaction equation

HRID 457938 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([CH:10]=1)[C:7](O)=[O:8].S(Cl)([Cl:14])=O>CCCCCCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([Cl:14])=[O:8]

Participants

4

Reactant 2

HCID 94475-Chlorosalicylic AcidHCID 24386Thionyl Chloride

Product 1

HCID 128632335-Chloro-2-hydroxybenzoyl chlorideYield 99.3%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 5-chloro-2-hydroxy-benzoic acid (20.0 g, 116 mmol) in heptane (232 mL, 0.5 M) was treated with thionyl chloride (25.4 mL, 348 mmol) and heated to 60° C. for 6 h. After cooling to room temperature, the solution was concentrated under reduced pressure to give 5-chloro-2-hydroxy-benzoyl chloride as a thick yellow oil (22 g) which was used without further purification.

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a2eab2155d4c4b518cbf2bcd1b497a70
Source dataset
uspto-grants-2007_03
Patent number
US07189749B2

Linked notes

Loading…