4-Phenylbutanol

colourless liquid

4-Phenyl-1-butanol was used in synthesis of NK105, a paclitaxel-incorporating micellar nanoparticle formulation.

4-Phenyl-1-butanol is used as a reagent in the synthesis of substituted pyrrolidine-2-carboxylic acids which are used in the treatment of AT2 receptor function associated diseases.

4-Phenylbutanol can be produced 1) from Phenylacetaldehyde and Acetaldehyde by condensation, followed by hydrogenation and reduction of the unsaturated aldehyde. 2) from Phenylethyl magnesiumbromide plus Ethylene oxide in a Grignard type reaction.

Chemical and Pharmaceutical Bulletin, 31, p. 2607, 1983 DOI: 10.1248/cpb.31.2607
Journal of the American Chemical Society, 73, p. 124, 1951 DOI: 10.1021/ja01145a045

4-Phenyl-1-butanol is oxidized by ceric ammonium nitrate in acetonitrile to afford 2-phenyltetrahydrofuran. It undergoes cyclization in presence of phosphoric acid at high temperature to yield tetralin.

Add Zinc Chloride Anhydrous 1 gram in 250 milliliters of there-necked flasks, Acetyl Chloride 98Min. 78.5 grams stir lower tetrahydrofuran (THF) 72 grams that drip, the ice bath cooling is lower to drip off rear insulation 1 hour to maintain the temperature at below 30 degree, and the water pump underpressure distillation gets 4-butylene-chlorohydrin ethyl ester 145 grams, productive rate 96%, purity 99.5%.
 30 gram 4-butylene-chlorohydrin ethyl esters, 78 gram benzene add respectively in 250 milliliters the there-necked flask, stir lower 0 degree that is cooled to, and add 30 gram aluminum trichloride (anhydrous)s in batches, the control temperature 10 spend below.Add rear insulation and spend 3 hours 10, the vapor detection raw material reaction is complete.Reaction solution slowly poured in the trash ice be hydrolyzed, stirred 30 minutes, separate organic phase.Organic phase is water, saturated common salt water washing respectively, anhydrous magnesium sulfate drying.After reclaiming benzene, underpressure distillation gets product 27 grams, productive rate: 70%.Above-mentioned product 27 grams are dissolved in 60 ml methanol, add the 10 ml water solution that fill 6 gram sodium hydroxide, heated and stirred 1 hour reacts completely.Behind the Distillation recovery methyl alcohol, wash neutrality with water, a minute oil-yielding stratum gets 20 gram benzene butanols, productive rate 95%.