1,4-Dichlorobenzene → 1,2-Dichloro-3-(propan-2-yl)benzene

Participants

Reaction Steps

This experiment is carried out in the same manner as in Example 1, except that propylene is used instead of isopropyl bromide. A dry-ice condenser is used instead of coolant condenser and propylene is sparged below the liquid level through a sparger tube. Thus, 377.8 g (2.57 mole) of mixture consisting of 70% (264.6 g; 1.8 mole) m-dichlorobenzene, 30% (113.2 g; 0.77 mole) p-dichlorobenzene and 48.0 g (0.36 mole) AlCl3 are placed in a 4-neck, one-liter flask and to it 34 g (0.81 mole) propylene is sparged below the liquid level. The temperature of reaction mixture is kept below 10° C. After overnight isomerization, decomposition of the AlCl3 complex, the organic layer shows little alkylation: only 1 to 2% dichlorocumene is formed.

Provenance & Evidence