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0 °C

A mixture of 20 parts of m-bromo-α-methylbenzylalcohol and 16.8 parts of 3,4-dihydropyran is cooled in an ice-bath and there are added 2 drops of hydrochloric acid solution. The whole is stirred overnight at 0° C and then allowed to come to room temperature. The mixture is poured onto ether and shaken successively with a sodium hydrogen carbonate solution and twice with water. The organic layer is separated, dried, filtered and evaporated. The residue is distilled, yielding 2-(m-bromo-α-methylbenzyloxy)tetrahydropyran; bp. 168°-169° C at 12 mm. pressure.

1. temperatureis cooled in an ice-bath
2. customto come to room temperature
3. additionThe mixture is poured onto ether
4. customThe organic layer is separated
5. customdried
6. filtrationfiltered
7. customevaporated
8. distillationThe residue is distilled