1-Phenylethanol

1-Phenylethanol is the organic compound with the formula C6H5CH(OH)CH3. It is one of the most commonly available chiral alcohols. It is a colorless liquid with a mild gardenia-hyacinth scent. Phenylethanol is an aromatic alcohol, it has the role of mouse metabolite. It is a natural product and is found in Cichorium endivia, Castanopsis cuspidata and other organisms. 1-Phenylethanol is found in nature as a glycoside, together with its hydrolase β-primeverosidase in tea (Camellia sinensis) flowers. It is also reportedly present in cranberries, grapes, chives, Scottish spearmint oil, cheeses, cognac, rum, white wine, cocoa, black tea, filbert, cloudberries, beans, mushrooms, and endives. Racemic 1-phenylethanol is produced by the reduction of acetophenone by sodium borohydride. Alternatively, benzaldehyde can be reacted with methylmagnesium chloride or similar organometallic compounds to afford racemic 1-phenylethanol. Asymmetric hydrogenation of acetophenone by Noyori catalysts proceeds quantitatively (50 atm H2, room temperature, minutes) in >99% e.e. The organic oxidising agent ethylbenzene hydroperoxide yields 1-phenylethanol when reduced.