3, 4-Dichlorobenzyl chloride (39 g., 0.2 mole) was added over a period of 15 min. to a stirred mixture of 4-chlorophenol (184.3 g., 1.2 moles) and fused zinc chloride (2 g., 0.01 mole) at 100". This mixture was heated further at 150" for 4 hr. Fractional distillation of the reaction product gave 126.1 g. of unchanged 4-chlorophenol, bp 80-100"(0.4 mm.), and 50 g.(877,) of 2-(3, 4-dichlorobenzyl)-4-chlorophenol, bp 176-180"(0.3 mm.); mp 69-74'. ...
[Evans, Delme; Cracknell, Mark E.; Saunders, John C.; Smith, Christine E.; Williamson, W. R. Nigel; et al. Journal of Medicinal Chemistry, 1987 , vol. 30, # 8 p. 1321 - 1327]
