Water → HCID 22618899, compound

HRID 617605Notes

Reaction equation

HRID 617605 reaction equation
[OH-].[K+].[CH2:3]([C:5]([CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:20][CH:19]=1)([C:11]([O:13]CC)=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:4].O>C(O)C>[CH2:9]([O:8][C:6]([C:5]([CH2:3][CH3:4])([CH2:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)=[CH:22][CH:23]=1)[C:11]([OH:13])=[O:12])=[O:7])[CH3:10]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 22618889HCID 22618889, compound

Product 1

HCID 22618899HCID 22618899, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Potassium hydroxide (14 g) was added to a solution of diethyl 2-ethyl-2-(2-(4-(4-phenylbutyloxy)phenyl)ethyl)malonate (46 g) in ethanol (300 ml) and the mixture was refluxed under heating for 3.5 hours. The reaction mixture was poured into water and washed with isopropyl ether. After being acidified to pH 1 with concentrated hydrochloric acid, the aqueous layer was extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated brine and dried over anhydrous sodium sulfate, and the solvent was distilled away under reduced pressure to give the subject compound (23 g).

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 3.5 hours
  3. washwashed with isopropyl ether
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with a saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-52e3f944e5c7465d9df38bd3685e07c5
Source dataset
uspto-grants-1999_09
Patent number
US05948820

Reaction notes

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