Benzyl Chloride → HCID 20364866, compound

Participants

Reaction Steps

A slurry of sodium hydride (3.7 g of 62%, 0.096 mole) in benzene (100 ml) and xylene (100 ml) was stirred at ambient temperature while 5-hydroxy-2-(3-fluorophenyl)-1,3-dioxane (18.9 g, 0.096 mole) was added dropwise during 1 hour. This mixture was stirred 1 additional hour, then to it was added benzyl chloride (12.2 g, 0.096 mole) during 1/2 hour. The mixture was heated under reflux for 18 hours, cooled, filtered and the filtrate washed with water (2 × 200 ml). The washed solution was dried over magnesium sulfate and concentrated to give 19.7 g of oil which was distilled under 2 × 10-4 mm pressure to give three fractions distilling at bath temperature of 98°-119° C (cut 1); 119°-139° C (cut 2); and 139°-143° C (cut 3). Cut 2 (9.1 g) was found by nmr analysis to be a mixture of cis and trans-dioxanes and the corresponding dioxolane. Cut 3 (1.5 g, m.p. 70°-71° C) was found by nmr to be 100% cis-5-benzyloxy-2-(3-fluorophenyl)-1,3-dioxane and this cut was used in further studies.

Provenance & Evidence