Citronellal → HCID 2750578, compound

HRID 718512Notes

Reaction equation

HRID 718512 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][CH2:40][CH:41]=[C:42]([CH3:44])[CH3:43])[CH2:36][CH:37]=O>>[CH3:34][CH:35]([CH2:39][CH2:40][CH:41]=[C:42]([CH3:44])[CH3:43])[CH2:36][CH:37]=[CH:2][CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 3

HCID 7794CitronellalHCID 10863251Phenethyltriphenylphosphonium bromideHCID 178418339Butyllithium

Product 1

HCID 2750578HCID 2750578, compoundYield 51.4%

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 3,7-dimethyloct-6-enal (1.80 g, 11.7 mmol, 1.5 equiv.), 0.97 g (51%) of the title compound as a colorless oil was obtained after purification by flash chromatography on SiO2 (cyclohexane).

Sources & evidence

ORD record
ord-ade6301995004f1e8e47777aa45dd619
Source dataset
uspto-grants-2015_11
Patent number
US09193935B2

Reaction notes

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