6459. Neophyl Chloride

Nomenclature

CAS number: 515-40-2
(2-Chloro-1,1-dimethylethyl)benzene; 1-chloro-2-methyl-2-phenylpropane; (β-chloro-tert-butyl)benzene.
C10H13Cl; mol wt 168.66.
C 71.21%, H 7.77%, Cl 21.02%.

Description and references

Prepn (68% yield) from benzene and methallyl chloride in the presence of concd sulfuric acid: Whitmore et al., J. Am. Chem. Soc. 65, 1469 (1943); Smith, Sellas, Org. Synth. coll. vol. IV, 702 (1963).

Chemical structure

Properties

Liquid. d425 1.0379. bp741 221° (dec); bp90 111°; bp30 120°; bp20 105°; bp18 104°; bp13 97°; bp10 95°; bp1.0 53°. nD20 1.5249; nD25 1.5228. Considerably less reactive with sodium than neopentyl chloride. Forms a Grignard reagent readily and in good yield. Salt effect in acetolysis: Fainberg, Winstein, J. Am. Chem. Soc. 78, 2763 (1956).