Isobutylene → 1-Chloro-3-(1,1-dimethylethoxy)-propane

Participants

Reaction Steps

A three-necked, 3-liter Morton flask was equipped with a mechanical stirrer, a Claisen adapter, a thermocouple, a dry-ice condenser with a gas inlet, and a dip tube. The glassware was dried in an oven at 125° C. overnight, assembled hot, and purged under argon until cool. The reaction flask was then charged with Amberlyst® 15 resin (42.0 grams), 3-chloro-1-propanol (4.65 moles, 1 equivalent, 440.0 grams), and pentane (3.7 equivalents, 2000 mL). These reagents were stirred at 500 RPMs. The alcohol was not completely soluble in the organic solvent. A cylinder of 2-methylpropene was attached to the dip tube and 261.16 grams (4.65 moles, 1 equivalent) was fed into the reaction vessel. The feed rate was approximately 2 grams/min. As the conversion of starting alcohol material into product proceeded, the reaction mixture became one liquid phase. The formation of the product was monitored via Gas Chromatography. After all the starting material was consumed, the solution was then pumped into a pressure filter where the Amberlyst® resin catalyst was separated from the product. The resin was washed with fresh pentane (2×100 ml.). The product was purified by distillation from 20 grams of potassium carbonate through a twelve inch Vigreaux column, under reduced pressure. This afforded a clear, colorless oil, yield=598.82 grams (83.75%). Boiling Point=64° C. at 60 mm Hg. GC assay=0.00% 2-methylpropene, 0.81% pentane, 1.13% 3-chloro-1-propanol, and 98.06% desired product. NMR(CDCl3): 3.63 (t, J=6 Hz, 2H), 3.46 (t, J=6 Hz, 2H), 2.28-1.62 (m, 2H), and 1.21 (s, 9H) ppm.

Provenance & Evidence