Water → HCID 14739700, compound

HRID 2254367Notes

Reaction equation

HRID 2254367 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[C:8]([CH:32]=[CH:33][CH:34]=1)[O:9][C:10]1[CH:11]=[CH:12][C:13]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[C:14]([CH2:16][CH2:17][C:18]([OH:20])=[O:19])[CH:15]=1)=[O:5])C.[OH-].[K+].O>C(O)C>[C:4]([C:6]1[CH:7]=[C:8]([CH:32]=[CH:33][CH:34]=1)[O:9][C:10]1[CH:11]=[CH:12][C:13]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[C:14]([CH2:16][CH2:17][C:18]([OH:20])=[O:19])[CH:15]=1)([OH:5])=[O:3]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 14739699HCID 14739699, compound

Product 1

HCID 14739700HCID 14739700, compoundYield 41.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 510 mg of 5-(3-ethoxycarbonylphenoxy)-2-(decyloxy)benzenepropanoic acid in 20 ml of ethanol was treated with an excess of potassium hydroxide in a small amount of water. After stirring for 18 hours, the solution was concentrated in vacuo. Diethyl ether and water added, the layers were separated, and the aqueous layer was acidified with lN hydrochloric acid. The aqueous layer was extracted with diethyl ether, and this extract was dried over sodium sulfate and concentrated in vacuo. Two crystallizations from ethyl acetate/hexane provided 200 mg of the desired title product, m.p. 102°-104° C.

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. additionDiethyl ether and water added
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with diethyl ether
  5. dry with materialthis extract was dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customTwo crystallizations from ethyl acetate/hexane

Sources & evidence

ORD record
ord-58d9f8423c424d7ba3583999a9508e65
Source dataset
uspto-grants-1993_08
Patent number
US05235064

Reaction notes

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