Phenothiazine → Ethyl Acrylate

Participants

Reaction Steps

2-(1,7,7-trimethylbicyclo[2.2.1]hept-2-yloxy)ethyl-2-propenoate (IX) was prepared by trans-esterification of 2-(Beta-hydroxyethoxy)-bornane (VII) with ethyl acrylate (VIII) using tetraisopropyl titanate catalyst. 125 g. of (VII), 221 g. ethyl acrylate (VIII), 0.90 g. phenothiazine, and 0.23 g. nitrobenzene were charged to a 500 ml. glass reactor equipped with magnetic stirrer, thermometer, 1"×12" packed column (stainless steel ProPac) and a distillation head equipped with a reflux control connected to a timer and temperature controller. A nitrogen stream was maintained in the condenser to prevent moisture from entering the system. The reactor was heated to reflux to remove any water as an ethanol/water azeotrope. After 2 hours refluxing, the reaction was cooled to 30° and 1.0 g. of tetraisopropyl titanante was added to the still pot. The reaction was heated to reflux at atmospheric pressure and ethanol removed as formed as its azeotrope with ethylacrylate up to 88° C. boiling range. When the boiling range reached 100° C. at atm., a cut was taken at 100 mm to 125° pot, then 10 mm to 125° pot. The product (IX) was distilled at 1 mm to 180° pot. 113 g. product (IX) analyzing at 98.4% by VPC was obtained. Structure was verified by NMR. Theory yield was 71%.

Provenance & Evidence