. C6 H6 • CH2 • CH2 • CH2 OH.

As cinnamic acid ester, normal phenylpropyl alcohol has been found in several resins and balsams, e. g. in Sumatra benzoes, in Oriental and American styrax and in the Honduras balsam which is frequently misnamed white Peru balsam. Probable is likewise its occurrence as cinnamate in xanthorrhoea resin and as acetate in cassia oil.

The phenylpropyl alcohol isolated from the above named resins is always accompanied by cinnamic alcohol from which it cannot be separated completely by fractionation. According to the method patented by Schimmel & Co.1) it can be obtained in a pure state by heating the mixture of alcohols with an equal part of concentrated formic acid. The cinnamic alcohol is thus resinified whereas the phenylpropyl alcohol is converted into the formate. The ester can be distilled with steam and then saponified.

Synthetically phenylpropyl alcohol can be obtained by the reduction of cinnamic alcohol with sodium amalgam in the presence of much water;2) or, according to the method of Bouveault and Blanc,3) by the reduction of cinnamic acid ester or the benzylacetic acid ester with sodium and absolute alcohol.

Phenylpropyl alcohol is a colorless, thick liquid possessing a faint peculiar odor resembling somewhat that of cinnamic alcohol and reminding of certain species of hyacinth. In ordinary solvents it is readily soluble. It is soluble in all proportions in 70 p. c. alcohol, in 1,5 vols of 60 p. c. alcohol and in about 3 vols, of 50 p. c. alcohol. In water it is not soluble in the ratio of 1:300.

1) G. I. P. 116091. Comp. Chem. Zentralbl. 1901, I. 69.

2) Rugheimer, Liebig's Annalen 172 (1874), 123. Comp. also Hatton and Hodgkinson, Chem. News 43 (1881), 1930; Chem. Zentralbl. 1881, 407.

3) G. I. P. No. 164294.

In the above mentioned patent, Schimmel & Co. record the following constants:

B. p. 235°, resp. 119° (12 mm.); d15o1,007.

When oxidized with chromic acid in glacial acetic acid, it yields hydrocinnamic acid (m. p. 49°). It can be more readily identified by its phenylurethane1) melting at 47 to 48°.