Dimethyl Sulfide → HCID 10976275, compound

Into a 3-neck 5-liter flask were weighed 1161.6 g (20 moles) of allyl alcohol, 950 g (15.3 moles) of dimethyl sulfide, and 1829 g (10 moles) of 48% aqueous tetrafluoroboric acid. The flask was attached to a large (1.5 liter) capacity Dean-Stark trap (initially filled with dimethyl sulfide) which was attached to a condenser. Reflux was started and an aqueous phase began to accumulate at the bottom of the Dean-Stark trap, displacing dimethyl sulfide back into the reaction mixture. Reflux was continued for six days. At the end of this period, the rate of accumulation of aqueous phase had become very small. The aqueous phase was drained into a tared bottle and weighed; the net weight of the aqueous phase was 1136.7 g. Excess dimethyl sulfide and allyl alcohol were allowed to distill at atmospheric pressure into the Dean-Stark trap until the temperature in the flask had reached 100° C. At this point, the flask was connected to a dry ice trap and vacuum was applied. The mixture in the flask was evaporated at 70° C. under magnetic stirring for one hour, with the pressure decreasing to a final value of 200 Pa. The yield of nonvolatile product was 1952 g. The nonvolatile product (identified as VII) was a viscous liquid containing a small amount of crystals. It showed no signs of further crystallization on standing at room temperature.

1. customInto a 3-neck 5-liter flask were weighed
2. customwas attached to a condenser
3. temperatureReflux
4. temperatureReflux
5. distillationto distill at atmospheric pressure into the Dean-Stark trap until the temperature in the flask
6. customhad reached 100° C
7. customAt this point, the flask was connected to a dry ice trap
8. customThe mixture in the flask was evaporated at 70° C.
9. additioncontaining a small amount of crystals
10. customno signs of further crystallization
11. customon standing at room temperature

ORD record

ord-7efcc703940c4fd3a615154701d3cb65

Source dataset

uspto-grants-1986_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04579931