Cyclohexyl methyl ketone → 3-(4-Benzyloxy-phenyl)-1-cyclohexyl-prop-2-en-1-one

HRID 356452

Reaction equation

HRID 356452 reaction equation
[CH3:1][C:2]([CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)=[O:3].[CH2:10]([O:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[OH-].[Ba+2].[OH-]>CCO>[CH2:10]([O:17][C:18]1[CH:19]=[CH:20][C:21]([CH:22]=[CH:1][C:2]([CH:4]2[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]2)=[O:3])=[CH:24][CH:25]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 13207Cyclohexyl methyl ketoneHCID 78109Benzaldehyde, 4-(phenylmethoxy)-HCID 6093286Barium hydroxide

Product 1

HCID 4714773-(4-Benzyloxy-phenyl)-1-cyclohexyl-prop-2-en-1-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was prepared as described in General Method 2 using 17.40 g (138 mmol) of cyclohexyl methyl ketone, 29.26 g (138 mmol) of 4-benzyloxybenzaldehyde, 3.17 g of barium hydroxide (anhydrous), and 300 mL of 95% EtOH. The reaction was heated at reflux for eight hours. The crude product was recrystallized from EtOAc. The 25.85 g of product, contaminated with some 4-benzyloxybenzaldehyde, was taken on without further purification.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for eight hours
  3. customThe crude product was recrystallized from EtOAc
  4. customwas taken on without further purification

Sources & evidence

ORD record
ord-8e577549f35c46388dfd37bc0e3e764c
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Linked notes

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