Water → HCID 13338866, compound

HRID 652460Notes

Reaction equation

HRID 652460 reaction equation
[C:1]([C:4]1[CH:23]=[CH:22][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]#N)=[CH:15][C:14]=2[Cl:21])=[C:6]([CH2:24][CH2:25][CH3:26])[C:5]=1[OH:27])(=[O:3])[CH3:2].[OH-:28].[K+].[OH2:30]>C(O)C>[C:1]([C:4]1[CH:23]=[CH:22][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([OH:30])=[O:28])=[CH:15][C:14]=2[Cl:21])=[C:6]([CH2:24][CH2:25][CH3:26])[C:5]=1[OH:27])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 13338859HCID 13338859, compound

Product 1

HCID 13338866HCID 13338866, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-(4-acetyl-3-hydroxy-2-n-propylphenoxy)-3-(2-chloro-4-cyanophenoxy)propane (1 g), potassium hydroxide (2 g), water (5 ml) and ethanol (10 ml) was refluxed for 4 hours, then concentrated, acidified with dilute hydrochloric acid and extracted with ethyl acetate. The extract was dried over sodium sulfate, the solvent was distilled off and the residue was recrystallized from ethyl acetate to give 4-[3-(4-acetyl-3-hydroxy-2-n-propylphenoxy)propoxy]-3-chlorobenzoic acid as crystals (780 mg). Melting point 171°-172° C.

Workup

  1. temperaturewas refluxed for 4 hours
  2. concentrationconcentrated
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extract was dried over sodium sulfate
  5. distillationthe solvent was distilled off
  6. customthe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-6182028e8969431983949c26b6e0d62c
Source dataset
uspto-grants-1987_06
Patent number
US04672073

Reaction notes

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