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

HRID 1003807Notes

Reaction equation

HRID 1003807 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-62c3f2b409b7437bb8b2f41c43f136a0
Source dataset
uspto-grants-2000_04
Patent number
US06046355

Reaction notes

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