p-Toluenesulfonic acid → HCID 12803567, compound

HRID 1461962Notes

Reaction equation

HRID 1461962 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:16])=[C:6]([CH:15]=1)[NH:7][C:8](=[O:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10].[C:17]1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)CC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:16])=[C:6]([CH:15]=1)[NH:7][C:8](=[O:14])[C:9]([O:11][CH2:12][CH2:13][CH3:17])=[O:10]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 12803542HCID 12803542, compound

Product 1

HCID 12803567HCID 12803567, compoundYield 300.7%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2.5 g of ethyl 5-chloro-2-hydroxyoxanilate, 200 mg of p-toluenesulfonic acid, and 100 ml of n-propanol was stirred for 2 days at 100° C. The reaction mixture was concentrated under reduced pressure and the residue was washed with ether and recrystallized from n-propanol to provide 0.9 g of n-propyl 5-chloro-2-hydroxyoxanilate.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. washthe residue was washed with ether
  3. customrecrystallized from n-propanol

Sources & evidence

ORD record
ord-5f501fcdcb024ca4a9cc825c70cb55cf
Source dataset
uspto-grants-1984_07
Patent number
US04457872

Reaction notes

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