1-Butanol → HCID 19261375, compound

Participants

Reaction Steps

2.16 g (93.9 mmol) of sodium are dissolved in 15 ml of n-butanol at 110° C. for 3 hours. 20 ml of dimethylformamide are added at ambient temperature and then the medium is degassed several times. 3.4 g (34.1 mmol) of copper(I) chloride are added at ambient temperature and then the reaction medium is stirred for 10 minutes. 6.2 g (31 mmol) of 3-bromo-4-hydroxybenzaldehyde are added and then the reaction medium is stirred at 120° C. for 2 hours. The reaction mixture is cooled to ambient temperature and then the reaction is halted by the addition of 50 ml of a 2M hydrochloric acid solution. The medium is extracted with 250 ml of ethyl acetate. The solvents are evaporated and then the residue is filtered through a silica gel patch (2 cm): eluent heptane/ethyl acetate 8/2. After evaporation of the solvents, 5.55 g of orange oil are obtained. This oil is crystallized from pentane. 4.8 g of 3-butoxy-4-hydroxybenzaldehyde are obtained in the form of a brown solid after filtration.

Provenance & Evidence