Bromocyclopentane → Tert-butyl 2-cyclopentyl-2-(4-methylphenyl)acetate

Participants

Reaction Conditions

Reaction Steps

33.5 g (0.3 mol) of potassium tert-butoxide are initially introduced into 100 ml of DMF at 0° C. with exclusion of moisture, and 51.6 g (0.25 mol) of tert-butyl 4-methylphenylacetate in 250 ml of DMF are added dropwise. The mixture is stirred at 0° C. for 30 min and 32.2 ml (0.3 mol) of cyclopentyl bromide in 150 ml of DMF are added dropwise at 5°-15° C. and the mixture is stirred at 25° C. for 20 h. After concentration, the residue is partitioned between water/diethyl ether, and the ether phase is dried over sodium sulphate and concentrated. The product crystallises out. Yield: 67 g (97.5% of theory) Solidification point: 51°-53° C.

Provenance & Evidence