Hydrogen Bromide → Tricyclo(3.3.1.1'3,7)dec-1-ylmethanol

Participants

Reaction Steps

To 39 g (0.17 moles) of zinc bromide, 29.8 g (0.17 mole) of hydrobromic acid were added. To the solution thus obtained, 11.5 g (0.069 mole) of 1-adamantyl methylalcohol which was prepared by the method shown in (1) was added and the mixture was refluxed for 11 hours. After the reaction mixture was brought to room temperature, 200 ml of water were added to this and extracted with two 300 ml portions of ether. After washing with 100 ml of water saturated with sodium bicarbonate and 100 ml of water, the resulting ether layer was dehydrated with anhydrous magnesium sulfate and was filtered. Ether was then distilled away. Residual solids were recrystallized from methanol or sublimed (1 mmHg, 75° C) to purify it, and 13 g of 1-adamantyl methyl bromide were obtained. Melting point of the product was 37°-39° C and the yield was 84%.

Provenance & Evidence