Potassium Hydroxide → 4-(3-Benzyloxy-phenoxy)-4-phenyl-butyric acid

HRID 322875Notes

Reaction equation

HRID 322875 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:27]=[CH:28][CH:29]=1)[O:12][CH:13]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:14][CH2:15][C:16]([O:18]CC)=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>CO>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:27]=[CH:28][CH:29]=1)[O:12][CH:13]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[CH2:14][CH2:15][C:16]([OH:18])=[O:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 23204045ethyl (RS)-4-(3-benzyloxyphenoxy)-4-phenylbutanoate

Product 1

HCID 220102084-(3-Benzyloxy-phenoxy)-4-phenyl-butyric acidYield 59.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of ethyl (RS)-4-(3-benzyloxy-phenoxy)-4-phenylbutanoate (1 g), aqueous potassium hydroxide solution (5 mL;10% w/v) and methanol (50 mL) is stirred at reflux for 30 minutes. The reaction mixture is then evaporated to dryness and the residue is partitioned between ethyl acetate (100 mL) and dilute hydrochloric acid (50 mL; 1 N). The organic layer is washed with water, dried over magnesium sulphate, filtered and concentrated under reduced pressure to give a brown oil, which slowly crystallises. Recrystallisation from cyclohexane gives (RS)-4-(3-benzyloxyphenoxy)-4-phenylbutanoic acid (0.55 g), in the form of a beige solid, m.p. 100-104° C. [Elemental analysis:- C,76.3;H,6.21%; Calculated:- C,76.2;H,6.12%].

Workup

  1. temperatureat reflux for 30 minutes
  2. customThe reaction mixture is then evaporated to dryness
  3. customthe residue is partitioned between ethyl acetate (100 mL) and dilute hydrochloric acid (50 mL; 1 N)
  4. washThe organic layer is washed with water
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give a brown oil, which
  9. customslowly crystallises
  10. customRecrystallisation from cyclohexane

Sources & evidence

ORD record
ord-00925cbaca7e44f5b72b9ca590d53ed2
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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