Acetophenone → Benzene, 1,1'-(1-methyl-1-propene-1,3-diyl)bis-

HRID 718514Notes

Reaction equation

[Br-].[CH2:2]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Li]CCCC.[C:34]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)(=O)[CH3:35]>>[CH2:34]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH:35]=[C:3]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH3:2]

Participants

Reactant 3

HCID 7410Acetophenone

HCID 10863251Phenethyltriphenylphosphonium bromide

HCID 178418339Butyllithium

Product 1

HCID 5096515Benzene, 1,1'-(1-methyl-1-propene-1,3-diyl)bis-Yield 46.3%

Procedure

Starting from phenethyltriphenylphosphonium bromide (3.48 g, 7.78 mmol, 1.0 equiv.), n-BuLi (1.6 M in hexanes, 4.9 mL, 7.78 mmol, 1.0 equiv.) and acetophenone (1.40 g, 11.7 mmol, 1.5 equiv.), 0.75 g (46%) of the title compound as a colorless oil was obtained after purification by flash chromatography on SiO2 (cyclohexane).

Sources & evidence

ORD record: ord-f96bd5b56dc448688f6cd024c365ab79
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193935B2

Reaction notes

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