2-[4-(2,2-Dimethylbenzo[d]1,3-dioxolan-5-oxy)butoxy]-1,3-dichloro-5-(phenylmethoxy)benzene → 4-[4-(2,2-Dimethylbenzo[d]1,3-dioxolan-5-yloxy)butoxy]-3,5-dichlorophenol

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Reaction Steps

As depicted in scheme 1, for example the known compound 2,6-dichloro-4-phenylmethoxyphenol (A) was reacted with a haloalkane of suitable chain length, such as 1-bromo-4-chlorobutane, under basic conditions, affording the corresponding 4-chlorobutoxy derivative (A1). Intermediate (A1) was in turn was reacted under basic conditions with the known hydroxy compound 2,2-dimethylbenzo[d]1,3-dioxolan-4-ol yielding the corresponding coupled compound 2-[4-(2,2-dimethylbenzo[d]1,3-dioxolan-5-oxy)butoxy]-1,3-dichloro-5-(phenylmethoxy)benzene (A2). Intermediate (A2) wha then treated with hydrogen gas under catalytic hydrogenation conditions, providing the deprotected intermediate 4-[4-(2,2-dimethylbenzo[d]1,3-dioxolan-5-yloxy)butoxy]-3,5-dichlorophenol (A3). Intermediate (A3) was then reacted with 1,1,1,3-tetrachloropropane, affording a compound of formula I, such as 5-(3,3-Dichloroprop-2-enyloxy)-2-[4-(2,2-dimethylbenzo[d]1,3-dioxolan-4-yloxy)butoxy]-1,3-dichlorobenzene. Example 1 set forth below describes in detail the method by which compounds of formula I were prepared as shown in scheme 1.

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