Chloroacetone → HCID 66806507, compound

A mixture of 4-isopropyl-thiophenol (5.0 g, 32.8 mmol), chloroacetone (7.0 mL, 88 mmol) and K2CO3 (6.4 g, 46.3 mmol) in acetone (100 mL) was refluxed over night. More K2CO3 (2 g, 14.5 mmol) and chloroacetone (3.5 mL, 43 mmol) were added and the reaction mixture was heated for another 5 h. The reaction mixture was filtered and the solvent was evaporated. The crude product was mixed with polyphosphoric acid (15 g) and chlorobenzene (100 mL) and the reaction mixture was heated at reflux for 5 h. (Plé et al., (1988) J. Heterocyclic Chem. 25, 1271-1272). The reaction mixture was diluted with CH2Cl2 and washed with water. The combined organic phases were dried and the solvent was evaporated. The crude product was purified on silica using heptane as eluent, giving 4.2 g of the title compound as a colourless oil (67% over two steps). 1H NMR (400 MHz, CDCl3) δ ppm 1.37 (d, 6 H) 2.47 (d, 3 H) 3.02-3.16 (m, 1 H) 7.08 (s, 1 H) 7.27-7.30 (m, 1 H) 7.58 (d, 1 H) 7.80 (d, 1 H).

1. temperaturewas refluxed over night
2. temperaturethe reaction mixture was heated for another 5 h
3. filtrationThe reaction mixture was filtered
4. customthe solvent was evaporated
5. additionThe crude product was mixed with polyphosphoric acid (15 g) and chlorobenzene (100 mL)
6. temperaturethe reaction mixture was heated
7. temperatureat reflux for 5 h. (Plé et al., (1988) J. Heterocyclic Chem. 25, 1271-1272)
8. additionThe reaction mixture was diluted with CH2Cl2
9. washwashed with water
10. customThe combined organic phases were dried
11. customthe solvent was evaporated
12. customThe crude product was purified on silica

ORD record

ord-11d688a4aee443e88325fce088e7af07

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09233946B2