Methanol → Methyl trans-3-Thiocyanoacrylate

To a stirred solution of ammonium thiocyanate (7.2 g., 0.095 mole) in 4N sulfuric acid solution (50 ml) at 40° C., a solution of trans-3-chloroacrylic acid (10.0 g., 0.095 mole) in 35 ml of methanol was added dropwise within 5 minutes. The mixture was refluxed for 18 hours, cooled and poured into water which was extracted thoroughly with ether. The ether extract was washed with saturated sodium bicarbonate solution and then with water. After drying (MgSO4), the solution was concentrated to give an oil which distilled at 70° C./0.3 mm; yield, 7.2 g.;

1. temperatureThe mixture was refluxed for 18 hours
2. temperaturecooled
3. extractionwas extracted thoroughly with ether
4. extractionThe ether extract
5. washwas washed with saturated sodium bicarbonate solution
6. dry with materialAfter drying (MgSO4)
7. concentrationthe solution was concentrated
8. customto give an oil which
9. distillationdistilled at 70° C./0.3 mm
10. customyield

ORD record

ord-2a0f1476494b4fd681a6aa6e49408237

Source dataset

uspto-grants-1994_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05302592