Citral → ((4E)-5,9-Dimethyldeca-2,4,8-trienyl)benzene

HRID 718511Notes

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]/[C:35](/[CH2:39][CH2:40][CH:41]=[C:42]([CH3:44])[CH3:43])=[CH:36]\[CH:37]=O>>[CH3:34]/[C:35](/[CH2:39][CH2:40][CH:41]=[C:42]([CH3:44])[CH3:43])=[CH: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 638011Citral

HCID 10863251Phenethyltriphenylphosphonium bromide

HCID 178418339Butyllithium

Product 1

HCID 86702761((4E)-5,9-Dimethyldeca-2,4,8-trienyl)benzeneYield 29%

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 (E)-3,7-dimethylocta-2,6-dienal (1.78 g, 11.7 mmol, 1.5 equiv.), 0.54 g (29%) of the title compound as a light yellow oil was obtained after purification by flash chromatography on SiO2 (cyclohexane).

Sources & evidence

ORD record: ord-18138ae648174741b69593df5a40b3c2
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193935B2

Reaction notes

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