Water → (4-Chloro-1,2-phenylene)dimethanol

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A solution of 4-chlorophthalic anhydride (24.83 g, 136.01 mmol) in tetrahydrofuran (100 mL) is added dropwise to a mechanically stirred suspension of LAH (8.72 g, 229.78 mmol) in tetrahydrofuran (500 mL). After stirring overnight at room temperature, the excess LAH is decomposed by cautious addition of water (8.5 mL), 10% aqueous NaOH (17 mL) and water (8.5 mL). The reaction is diluted with tetrahydrofuran (300 mL) and the solids are removed by filtration through a celite pad and washed with tetrahydrofuran. The combined filtrate and wash is concentrated in vacuo on a rotary evaporator to afford diol 257 as a colorless liquid (22.16 g) that crystallized on standing. Crystallization is effected in benzene. [O. Farooq, Synthesis, 1035-1036 (1994); R. F. Bird, E. E. Turner, J. Chem. Soc. 5050-5051 (1952); J. Tirouflet, Compt. rend., 238, 2246-2247 (1954)]

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