3,5,5-Trimethylhexanal → (5,7,7-Trimethyloct-2-enyl)benzene

HRID 718525Notes

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.[CH3:34][CH:35]([CH2:39][C:40]([CH3:43])([CH3:42])[CH3:41])[CH2:36][CH:37]=O>>[CH3:34][CH:35]([CH2:39][C:40]([CH3:43])([CH3:42])[CH3:41])[CH2:36][CH:37]=[CH:2][CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

Reactant 3

HCID 215743,5,5-Trimethylhexanal

HCID 10863251Phenethyltriphenylphosphonium bromide

HCID 178418339Butyllithium

Product 1

HCID 86702771(5,7,7-Trimethyloct-2-enyl)benzeneYield 65.2%

Procedure

Starting from phenethyltriphenylphosphonium bromide (2.80 g, 6.26 mmol, 1.0 equiv.), n-BuLi (1.6 M in hexanes, 3.9 mL, 6.26 mmol, 1.0 equiv.) and 3,5,5-trimethylhexanal (1.33 g, 9.39 mmol, 1.5 equiv.), 0.94 g (65%) of the title compound as a colorless oil was obtained after purification by flash chromatography on SiO2 (cyclohexane/EtOAc 997:3).

Sources & evidence

ORD record: ord-340e9598e2b9495f8e00128b130f33e8
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193935B2

Reaction notes

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