Ethyl Thioglycolate → HCID 18387351, compound

Sodium (9.06 g; 0.39 mole) was decomposed in allyl alcohol (380 ml). The obtained solution was treated by dropwise adding of first ethyl mercaptoacetate (42.7 ml; 0.39 mole) at the temperature of 0° C. and then of allyl 4-chlorobutyrate (58.3 g; 0.36 mole) prepared according to the process disclosed in Example 2a. The obtained mixture was stirred for three hours at room temperature and then for 1 hour at reflux temperature. The mixture was concentrated by evaporation and poured into a mixture of diethylether (200 ml) and of an ice/water mixture (100 g). The obtained solution was acidified with 1M hydrochloric acid solution to achieve a pH value of the medium between 3 and 6. The ether phase was separated and the obtained aqueous phase was extracted with diethyl ether (200 ml). The combined ether fractions were washed with water (200 ml) and 4% aqueous sodium hydrogencarbonate solution (200 ml) and dried with magnesium sulfate. After the removal of the drying agent and evaporation of ether, the title compound (78.1 g; 84%) was obtained, which was used in the crude form in the next reaction.

1. additionThe obtained solution was treated
2. temperaturefor 1 hour at reflux temperature
3. concentrationThe mixture was concentrated by evaporation
4. additionpoured into a mixture of diethylether (200 ml) and of an ice/water mixture (100 g)
5. customThe ether phase was separated
6. extractionthe obtained aqueous phase was extracted with diethyl ether (200 ml)
7. washThe combined ether fractions were washed with water (200 ml) and 4% aqueous sodium hydrogencarbonate solution (200 ml)
8. dry with materialdried with magnesium sulfate
9. customAfter the removal of the drying agent and evaporation of ether

ORD record

ord-6529ee5d522d482bb354817a8784bd4b

Source dataset

uspto-grants-2002_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06489318B1