Cinnamoylbenzene → 2-(3-oxo-1,3-diphenylpropyl)cyclohexanone

HRID 990613Notes

Reaction equation

HRID 990613 reaction equation
[CH:1](=[CH:8][C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]1(=[O:23])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.[OH-].[Na+]>C(O)C>[C:2]1([CH:1]([CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22][C:17]2=[O:23])[CH2:8][C:9](=[O:10])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7189CinnamoylbenzeneHCID 7967CyclohexanoneHCID 14798Sodium Hydroxide

Product 1

HCID 2728562-(3-oxo-1,3-diphenylpropyl)cyclohexanone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Ten parts of benzalacetophenone and 5 parts of cyclohexanone was dissolved in 200 mL of ethyl alcohol and a solution of 5 parts of sodium hydroxide in 100 ml of ethanol was added to the reaction mixture. After 30 minutes the solution became cloudy and white solid was appeared. The reaction mixture was stirred for 10 hours at room temperature and solid was filtered, washed with water and then with 100 ml of ethyl alcohol. The white solid was dried under reduced pressure,with a yield of 12 parts. The reaction proceeded as follows:

Workup

  1. filtrationsolid was filtered
  2. washwashed with water
  3. dry with materialThe white solid was dried under reduced pressure,with a yield of 12 parts

Sources & evidence

ORD record
ord-872992daec6c4da09d88e3046d8c3c3d
Source dataset
uspto-grants-2002_10
Patent number
US06461876B1

Reaction notes

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