Potassium Hydroxide → 2-[4-(4-Chlorophenyl)-benzyloxy]-2-phenylpropionic acid

HRID 1105870Notes

Reaction equation

HRID 1105870 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:28]=[CH:27][C:11]([CH2:12][O:13][C:14]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)([CH3:20])[C:15]([O:17]CC)=[O:16])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[OH-].[K+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:28]=[CH:27][C:11]([CH2:12][O:13][C:14]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)([CH3:20])[C:15]([OH:17])=[O:16])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 20555297Ethyl 2-[4-(4-chlorophenyl)benzyloxy]-2-phenylpropionate

Product 1

HCID 205552882-[4-(4-Chlorophenyl)-benzyloxy]-2-phenylpropionic acidYield 47.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl 2-[4-(4-chlorophenyl)benzyloxy]-2-phenylpropionate (7.9 g.) in methanol (100 ml.) containing potassium hydroxide (11.0 g.) was heated under reflux for 2 hours and then evaporated. The residue was partitioned between water (100 ml.) and ether (30 ml.). The aqueous phase was separated and acidified with 4 N-hydrochloric acid to pH 2-3 and extracted with ether (3×30 ml.). These ether extracts were washed with water, dried (MgSO4) and evaporated. The residue was crystallised by treatment with a mixture of ethyl acetate and hexane to give 2-[4-(4-chlorophenyl)-benzyloxy]-2-phenylpropionic acid, (3.5 g.), m.p. 125°-126° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. customevaporated
  4. customThe residue was partitioned between water (100 ml.) and ether (30 ml.)
  5. customThe aqueous phase was separated
  6. extractionextracted with ether (3×30 ml.)
  7. washThese ether extracts were washed with water
  8. dry with materialdried (MgSO4)
  9. customevaporated
  10. customThe residue was crystallised by treatment with a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-986e7356c4b346408530d035d1b301d8
Source dataset
uspto-grants-1982_01
Patent number
US04310544

Reaction notes

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