Water → HCID 57661144, compound

HRID 384597Notes

Reaction equation

HRID 384597 reaction equation
Br[C:2]([CH3:23])([CH3:22])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12][C:13]([O-:15])=[O:14])=[CH:7][CH:6]=1)=[O:4].[OH-:24].[Na+].O>COCCOC>[OH:24][C:2]([CH3:23])([CH3:22])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12][C:13]([OH:15])=[O:14])=[CH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 86629707HCID 86629707, compound

Product 1

HCID 57661144HCID 57661144, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 64.0 g (0.164 mol) of 3-[4-(2-bromo-2-methylpropionyl)phenyl]-3-phenylpropanoate, 13.2 g (0.328 mol) of sodium hydroxide, 70 ml of water, and 300 ml of 1,2-dimethoxyethane is heated at reflux for 16 hours. The reaction is concentrated, and then acidified with 25 ml of 1.5 N hydrochloric acid solution. Ethyl acetate (200 ml) is added, and the organic layer is washed with distilled water, dried over sodium sulfate, and concentrated. The crude product is passed through a pad of silica gel with ethyl acetate as the eluent to give 44 g (86% yield) of the title compound.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 16 hours
  3. concentrationThe reaction is concentrated
  4. additionEthyl acetate (200 ml) is added
  5. washthe organic layer is washed with distilled water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a4ebd80b93bb49b584a5c104fc38d1ed
Source dataset
uspto-grants-2013_02
Patent number
US08367743B2

Reaction notes

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