Salicylic Acid → Salicyloyl chloride

HRID 1087282Notes

Reaction equation

HRID 1087282 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].C(O)(=O)[C:8]1[C:9](=C[CH:12]=[CH:13][CH:14]=1)[OH:10]>C1C=CC=CC=1>[OH:10][C:9]1[CH:8]=[CH:14][CH:13]=[CH:12][C:1]=1[C:2]([Cl:4])=[O:3]

Participants

4

Reactant 2

HCID 338Salicylic AcidHCID 65578Oxalyl chloride

Product 1

HCID 74041Salicyloyl chloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

Add 11.8 g of oxalyl chloride dissolved in 25 ml of benzene to a suspension of 6.91 g of salicylic acid and 125 ml of benzene over a period of 20 minutes. Heat the mixture for about 14 hours, cool and evaporate the solvent to give 2-hydroxybenzenecarbonyl chloride as an oil. The crude product can be used directly in the subsequent step.

Workup

  1. temperatureHeat the mixture for about 14 hours
  2. temperaturecool
  3. customevaporate the solvent

Sources & evidence

ORD record
ord-46be588075fc42919e601021509339b3
Source dataset
uspto-grants-1991_07
Patent number
US05034531

Reaction notes

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