2,3,4,5-Tetraphenyl-2,4-cyclopentadien-1-one → 1,2,3,4-Tetraphenyl-5-p-vinylphenylcyclopenta-1,3-dien-5-ol

HRID 2220676Notes

Reaction equation

HRID 2220676 reaction equation
[C:1]1([C:7]2[C:11](=[O:12])[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[C:9]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:8]=2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:31]([C:33]1[CH:38]=[CH:37][C:36]([Mg]Br)=[CH:35][CH:34]=1)=[CH2:32]>CCOCC>[C:13]1([C:10]2[C:11]([C:36]3[CH:37]=[CH:38][C:33]([CH:31]=[CH2:32])=[CH:34][CH:35]=3)([OH:12])[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[C:8]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:9]=2[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 680682,3,4,5-Tetraphenyl-2,4-cyclopentadien-1-oneHCID 178436500HCID 178436500, compound

Product 1

HCID 692500951,2,3,4-Tetraphenyl-5-p-vinylphenylcyclopenta-1,3-dien-5-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

46.2 g (0.12 mol) of tetraphenylcyclopentadienone were reacted with 0.61 mol of p-vinylphenylmagnesium bromide in 400 ml of ether and then hydrolysis to yield 1,2,3,4-tetraphenyl-5-p-vinylphenylcyclopenta-1,3-dien-5-ol. (Elemental analysis for C37H28O: found: C, 90.91%, H, 5.75%. calculated: C, 90.85%, H, 5.78%).

Workup

  1. customhydrolysis

Sources & evidence

ORD record
ord-e12f7cf35730419aad2220a056a829ef
Source dataset
uspto-grants-2008_08
Patent number
US07417247B2

Reaction notes

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