3237. p,α-Dimethylbenzyl Alcohol

Nomenclature

CAS number: 536-50-5
α,4-Dimethylbenzenemethanol; p-tolylmethylcarbinol; methyl-p-tolylcarbinol; 4-(α-hydroxyethyl)toluene; 4-methyl-α-phenethyl alcohol; 1-p-tolyl-1-ethanol.
C9H12O; mol wt 136.19.
C 79.37%, H 8.88%, O 11.75%.

Description and references

Constituent of the essential oil from Curcuma longa L., Zingiberaceae and related plants: Dieterle, Kaiser, Arch. Pharm. 271, 337 (1933). Prepd from p-tolylmagnesium bromide and acetaldehyde in ether: v. Auwers, Kolligs, Ber. 55, 42 (1922); Eisenlohr, Schulz, Ber. 57, 1816 (1924); from 4-methylacetophenone: Gastaldi, Cherchi, Gazz. Chim. Ital. 45, II, 274 (1915).

Chemical structure

Properties

Viscous liquid. Odor somewhat like that of menthol. The natural product is probably levorotatory. Constants for the synthetic dl-form: d415.5 0.9668. bp756 219°; bp14 134°; bp11 115-116°. Very sparingly sol in water. Miscible with abs alcohol, ether. Also sol in isopropanol, liquid petrolatum.

Derivative

Phenylurethan.
C16H17NO2; mol wt 255.31.
C 75.27%, H 6.71%, N 5.49%, O 12.53%.

Properties

Crystals, mp 97.5°.