Ethanol → 4-Amino-5-chloro-2-hexyloxybenzoic acid

HRID 1608232Notes

Reaction equation

HRID 1608232 reaction equation
C[O:2][C:3](=[O:22])[C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([NH:11]C(=O)C)=[CH:6][C:5]=1[O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].C(O)C.[OH-].[Na+]>O>[NH2:11][C:7]1[C:8]([Cl:10])=[CH:9][C:4]([C:3]([OH:22])=[O:2])=[C:5]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:6]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 543884334-Acetylamino-5-chloro-2-hexyloxybenzoic acid methyl ester

Product 1

HCID 198486244-Amino-5-chloro-2-hexyloxybenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-acetylamino-5-chloro-2-hexyloxybenzoic acid methyl ester (2.1 g), ethanol (10 ml), and water (30 ml) containing sodium hydroxide (2.6 g) is heated under reflux for 4 hours. The ethanol is distilled off under reduced pressure, and the resulting solution is acidified with dilute hydrochloric acid and extracted with chloroform. The organic layer is treated in the same manner as in part (2) of this Reference Example to give the title compound.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 4 hours
  3. distillationThe ethanol is distilled off under reduced pressure
  4. extractionextracted with chloroform

Sources & evidence

ORD record
ord-5e470ed3857d4a37a5fc505cd19b65c3
Source dataset
uspto-grants-1989_09
Patent number
US04870074

Reaction notes

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