Potassium Hydroxide → 6-(4-Amino-2,6-dichlorophenoxy)hexanoic acid

HRID 1634250Notes

Reaction equation

HRID 1634250 reaction equation
C([NH:4][C:5]1[CH:19]=[C:18]([Cl:20])[C:8]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[C:7]([Cl:21])[CH:6]=1)(=O)C.[OH-].[K+]>CO.O>[NH2:4][C:5]1[CH:6]=[C:7]([Cl:21])[C:8]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[C:18]([Cl:20])[CH:19]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 186777696-(4-Acetylamino-2,6-dichlorophenoxy)hexanoic acid

Product 1

HCID 186777636-(4-Amino-2,6-dichlorophenoxy)hexanoic acidYield 66%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

7.5 g (22.4 mmol) of 6-(4-acetylamino-2,6-dichlorophenoxy)hexanoic acid in 140 ml of 1 m potassium hydroxide solution in methanol/water (3:1) were boiled under reflux overnight. The methanol was removed in a rotary evaporator, and the residue was diluted with about 30 ml of water and acidified to pH 5 with glacial acetic acid. The mixture was stirred in an ice bath for 30 minutes and then filtered with suction. The crude product was subjected to column chromatography using n-heptane/ethyl acetate=1/1 and produced 4.3 g (14.7 mmol, 66%) of the required product.

Workup

  1. temperatureunder reflux overnight
  2. customThe methanol was removed in a rotary evaporator
  3. additionthe residue was diluted with about 30 ml of water
  4. filtrationfiltered with suction

Sources & evidence

ORD record
ord-e37ee815ed9644319f5671898b839ab5
Source dataset
uspto-grants-2003_01
Patent number
US06506778B2

Reaction notes

Loading…