Water → HCID 86689404, compound

Participants

Reaction Conditions

Reaction Steps

Carbon tetrabromide (218 g, 657 mmol) is dissolved in anhydrous dichloromethane (1600 cm3) and cooled to 0° C. Triphenylphosphine (345 g, 1.32 mol) is added in one portion, the mixture exothermed to 15° C. and is re-cooled to 0° C., whilst stirring for 45 minutes. 2-Hexyldecan-1-al (Price, S. C.; Stuart, A. C.; You, W.; Macromolecules 2010, 43, 797-804) (79.0 g, 329 mmol) is added dropwise over 45 minutes and the mixture is allowed to warm to 23° C. After 2 hours, the reaction mixture is carefully poured into water (2000 cm3), the organic phase is separated, dried over sodium sulfate, filtered and concentrated in vacuo. The crude product is dissolved in dichloromethame (2000 cm3) and passed twice through a plug of silica eluting with petroleum ether (40-60° C.) to yield the title product as a pale yellow oil (117.4 g, Yield: 90%). NMR (1H, 400 MHz, CDCl3): δ 6.15 (d, J=9.6 Hz, 1H); 2.38 (m, 1H); 1.29 (m, 24H); 0.91 (m, 6H).

Provenance & Evidence