Potassium Hydroxide → 7-(4-Chlorophenyl)-2-(4-methylphenoxy)heptanoic acid

HRID 2107141Notes

Reaction equation

HRID 2107141 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([O:19][C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=2)[C:14]([O:16]CC)=[O:15])=[CH:4][CH:3]=1.[OH-].[K+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([O:19][C:20]2[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=2)[C:14]([OH:16])=[O:15])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 23047775HCID 23047775, compound

Product 1

HCID 1736087-(4-Chlorophenyl)-2-(4-methylphenoxy)heptanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 3.25 g (9 mmol) of ethyl 7-(4-chlorophenyl)-2-(4-methylphenoxy)heptanoate, 15 ml of 1N caustic potash solution and 45 ml of methanol is heated for 3 h, with stirring, at 40° C. Then the methanol is evaporated in vacuo, the aqueous solution is washed with ether and acidified with dilute hydrochloric acid. The precipitated oil is taken up in ether and the ether solution is dried and concentrated by evaporation. The residue is ground with ligroin. 2.7 g (86% of theory) is obtained of 7-(4-chlorophenyl)-2-(4-methylphenoxy)heptanoic acid, M.P. 74°-76° C.

Workup

  1. temperatureis heated for 3 h
  2. customThen the methanol is evaporated in vacuo
  3. washthe aqueous solution is washed with ether
  4. dry with materialthe ether solution is dried
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-0bfb3ef5458f4aa0be180c293fb11afc
Source dataset
uspto-grants-1990_06
Patent number
US04933367

Reaction notes

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