Water → HCID 68918222, compound

HRID 384601Notes

Reaction equation

HRID 384601 reaction equation
C([O:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][C:14]2([C:20]([C:22]2(Br)[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]2[C:28]2[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][O:36]C(=O)C)=[CH:30][CH:29]=2)=[O:21])Br)=[CH:9][CH:8]=1)(=O)C.[OH-:41].[Na+].[OH2:43]>COCCOC>[OH:36][CH2:35][CH2:34][C:31]1[CH:30]=[CH:29][C:28]([CH:23]2[CH2:24][CH2:25][CH2:26][CH2:27][C:22]2([C:20]([C:14]2([OH:43])[CH2:15][CH2:16][CH2:17][CH2:18][CH:13]2[C:10]2[CH:11]=[CH:12][C:7]([CH2:6][CH2:5][OH:4])=[CH:8][CH:9]=2)=[O:21])[OH:41])=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 68915143HCID 68915143, compound

Product 1

HCID 68918222HCID 68918222, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 8.19 g (23.2 mmol) of 4-(2-acetyloxyethyl)phenyl1-bromo-cyclohexyl ketone, 6.26g (15.65 mmol) of sodium hydroxide, 20 ml of water, and 50 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. 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 eluant to give 5.50 g of the title compound which is further purified by recystallization. Mass spectrum: m/z=249 (M+H).

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-1436cfc353e84de4b6ee11559f504e55
Source dataset
uspto-grants-2013_02
Patent number
US08367743B2

Reaction notes

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