Hydrochloric Acid → 1,4-Bis(3-hydroxy-2,2-dimethylpropyl)benzene

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Reaction Steps

To 500 ml of dry tetrahydrofuran was added 11.4 g of lithium aluminum hydride and 60 g of 1,4-bis(2-carbomethoxy-2-methylpropyl)benzene. The mixture was stirred overnight at room temperature. To the thick reaction mixture was added 300 ml of ethyl acetate, 30 ml of saturated aqueous NH4Cl, and 5 ml of concentrated HCl The mixture was stirred and filtered. Solvent was evaporated from the filtrate and the residue was recrystallized from benzene to obtain 20 g of 1,4-bis(3-hydroxy-2,2-dimethylpropyl)benzene. The solid from the above filtration was slurried with 50 ml of H2O, 20 ml of concentrated HCl, and 150 ml of benzene and heated at reflux for 1 hour. The benzene layer was then separated, dried over MgSO4 at 80° C, filtered hot and then cooled to precipitate an additional 10 g of 1,4-bis(3-hydroxy-2,2 -dimethylpropyl)benzene, m.p. 104°-105° C.

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