Sodium Hydroxide → 4-(Methoxymethoxy)-1,1-cyclohexanedimethanol

Participants

Reaction Steps

1.76 g of lithium aluminum hydride was suspended in 90 ml of tetrahydrofuran and ice-cooled. Then 11.1 g of diethyl 4-(methoxymethoxy)cyclohexane-1,1-dicarboxylate dissolved in 30 ml of tetrahydrofuran was dropped thereinto. After stirring for 40 minutes, 1.8 ml of water, 1.8 ml of 15% sodium hydroxide and 5.4 ml of water were successively added thereto so as to decompose the excessive reagent. After further adding anhydrous sodium sulfate and celite, the reaction mixture was stirred at room temperature, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluted with dichlorometheane/methanol) to thereby give 6.84 g of the title compound as a white solid.

Provenance & Evidence