3,7-Dimethyl-1-octanol → HCID 57815684, compound

Participants

Reaction Steps

1,4-Dibromobutane (22.7 g, 105 mmol), 3,7-dimethyloctanol (4.99 g, 31.5 mmol) and tetrabutylammonium bromide (585 mg, 1.81 mmol) were dissolved in hexane (40 mL). Sodium hydroxide solution (50% w/v, 40 mL) was added to the reaction mixture and then the whole was heated at reflux for 2 d. The reaction mixture was cooled to room temperature, diluted with hexane (40 mL) and water (40 mL) and transferred to a separatory funnel. The product was extracted into the organic layer and the aqueous layer was further extracted with ether (3×20 mL). The combined organic layers were dried (Na2SO4) and the solvent was removed under reduced pressure. The dibromobutane in the crude product was removed under reduced pressure and heating at 120° C. under high vacuum (Kugelrohr). This gave the product as a honey-coloured oil (6.24 g, 68%).

Provenance & Evidence