Res. Chem. Intermed.
, Vol. 28, No. 6, pp. 551–559 (2002)
Also available online - www.vsppub.com
Three-step synthesis of 1,1-dimethoxy-2-phenylpropane
, PETR KA
Laboratory of Industrial Chemistry, Process Chemistry Group, Åbo Akademi, Turku/Åbo, Finland
Department of Organic Technology, Institute of Chemical Technology,Prague, Czech Republic
Received 19 October 2001; accepted 9 April 2002
Abstract—In this work is presented a three-step synthesis of 1,1-dimethoxy-2-phenylpropane. The
performed procedure was based on epoxidationof 2-phenylpropeneto 2-methyl-2-phenyloxirane, acid
catalyzed rearrangement of oxirane to 2-phenylpropanal and acetalization of the aldehyde to 1,1-
dimethoxy-2-phenylpropane. The 1,1-dimethoxy-2-phenylpropane prepared was of high analytical
purity (99.8%) with corresponding sensory properties, which allow its usage in the food industry.
1,1-Dimethoxy-2-phenylpropane is an essential component of nut aromas, in par-
ticular, characteristic especially for the hazelnut aroma. Since one-step preparation
can be accomplished only with dif culties [1–3], the proposed three-step synthesis
of 2-phenylpropanal is based on well-known and routine processes. The proposed
procedure can be described by the following scheme.
Scheme 1. Three-step synthesis of 1,1-dimethoxy-2-phenylpropane.
In technical practice, the epoxidations of unsaturated compounds are frequently
carried out by means of organic peracids. The most commonly used one is peracetic
acid [4–11]. Another important epoxidation agent is hydrogen peroxide [12–16].
To whom correspondence should be addressed. E-mail: Libor.Cerveny@vscht.cz