Hydrochloric Acid → 2,6-Bis(3-hydroxy-2,2-dimethylpropyl)naphthalene

Participants

Reaction Steps

To a solution of 6.0 g of lithium aluminum hydride in 1 liter of dry tetrahydrofuran, 40 g of 2,6-bis(2-carbomethoxy-2-methylpropyl)naphthalene was added slowly. The reaction mixture thickened on stirring overnight. Then there was added 150 ml of ethyl acetate, 60 ml of saturated aqueous NH4Cl and 150 ml of concentrated HCl. After thorough mixing the solid and liquid were separated by filtration. The filtrate was evaporated to dryness and the residue was recrystallized from benzene to obtain about 20 g of 2,6-bis(3-hydroxy-2,2-dimethylpropyl)naphthalene. The solid from the above filtration was slurried with 50 ml of H2O, 10 ml of concentrated HCl and 50 ml of benzene and the mixture was heated at reflux for 1 hr. The benzene layer was separated, dried with MgSO4 at 80° C, filtered hot and then cooled to precipitate about 10 g of 2,6-bis(3-hydroxy-2,2-dimethylpropyl)naphthalene, m.p. 162°-165° C.

Provenance & Evidence