2-Cyclohexen-1-one → 6,7-Diphenyl-3,4,4a,5,8,8a-hexahydronaphthalen-1(2H)-one

HRID 351449Notes

Reaction equation

HRID 351449 reaction equation
[C:1]1([C:7]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH2:10])=[CH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17]1(=[O:23])[CH2:22][CH2:21][CH2:20][CH:19]=[CH:18]1>C1(C)C=CC=CC=1>[C:1]1([C:7]2[CH2:8][CH:21]3[CH:22]([CH2:10][C:9]=2[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:17](=[O:23])[CH2:18][CH2:19][CH2:20]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 135942-Cyclohexen-1-oneHCID 41291332,3-Diphenyl-1,3-butadiene

Product 1

HCID 184363646,7-Diphenyl-3,4,4a,5,8,8a-hexahydronaphthalen-1(2H)-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2,3-diphenyl-1,3-butadiene (2.772 g, 13.44 mmol) and cyclohex-2-enone (1 eq.) was refluxed in toluene (26 mL) for 48 h. The reaction mixture was then concentrated and purified on SiO2 (20% ethyl acetate/hexane) to yield 6,7-diphenyl-3,4,4a,5,8,8a-hexahydro-2H-naphthalen-1-one.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. custompurified on SiO2 (20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-60350ca1d4944c65a9d0968cd7b16b2d
Source dataset
uspto-grants-2007_02
Patent number
US07183445B2

Reaction notes

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