HCID 18004193, compound → HCID 18419918, compound

Participants

Reaction Steps

LiAlH4 (9.4 g, 248 mmol) was initially introduced in 300 ml of THF under N2. Dimethyl 2-(3′-(3,7-dimethyloctyloxy)phenyl)terephthalate (75.5 g, 177 mmol), dissolved in 120 ml of THF, was then slowly added dropwise at RT. The mixture was subsequently stirred under reflux for 4 hours and cooled. Excess LiAlH4 was then carefully destroyed by addition of H2O. Semiconcentrated H2SO4 was subsequently carefully added dropwise (about 50 ml). The batch was of very low viscosity at this point. After a subsequent stirring time of 1 hour, a clear solution and a gray precipitate at the bottom of the flask were observed. The clear solution was decanted off, and the solvent was stripped off. The precipitate which remained was stirred with plenty of water and ethyl acetate and filtered, the organic phase was separated off, the solvent was stripped off, and combined with the first organic phase. The combined organic phases were taken up in ethyl acetate and extracted five times with water. After the extracts had been dried over MgSO4, the solvent was stripped off. The resultant oil was stirred a number of times with hexane and dried in an oil-pump vacuum, giving the product as a pure, pale-yellow, high-viscosity oil (54 g, 82%).

Provenance & Evidence