Diethyl Ether → alpha,alpha-Dimethyl-cyclopentanepropanol

Temperature

5 °C

262.25 g (1.6 mol) of 3-cyclopentylpropionyl chloride (origin: Aldrich) and 500 ml of anhydrous THF (tetrahydrofuran) were charged into a 5 1 4-neck round bottom flask equipped with a mechanical stirrer and a reflux condenser. Upon cooling to 5° C., 3.2 1 of 1.4 M methyllitium in ether (4.48 mol) was added dropwise to the stirred solution at a rate which maintained the pot temperature between 15-25° C. The reaction mixture was then stirred at room temperature for 26 h and subsequently quenched, at 5° C., with the addition of 350 ml of water. The organic layer was separated and the ether and THF were stripped at reduced pressure. The resulting crude product was fractionally distilled with a 10-plate Oldershaw column at high vacuum to give 162 g of 4-cyclopentyl-2-methyl-2-butanol (purity>97%; yield=65%).

1. customequipped with a mechanical stirrer and a reflux condenser
2. temperaturemaintained the pot temperature between 15-25° C
3. customsubsequently quenched, at 5° C., with the addition of 350 ml of water
4. customThe organic layer was separated
5. distillationThe resulting crude product was fractionally distilled with a 10-plate Oldershaw column at high vacuum

ORD record

ord-472165d584f64ca398e7b6b566b5a18f

Source dataset

uspto-grants-2004_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06720295B2