Chloroacetone → HCID 14175765, compound

A mixture of 4-methoxythiophenol (2.8 g, 20 mmol), K2CO3 (5.5 g, 40 mmol) and chloroacetone (6.6 mL, 82 mmol) in acetone (50 mL) was heated at reflux over night. The reaction mixture was filtered and the solvent was evaporated giving 5.0 g crude product. The intermediate thioether was dissolved in chlorobenzene (50 mL) and polyphosphoric acid (PPA, 0.5 g) was added (Plé et al., (1988) J. Heterocyclic Chem. 25, 1271-1272). The reaction mixture was refluxed over night. The solvent was decanted and the PPA residue was treated with CH2Cl2. The combined organic extracts were washed with water and dried before the solvents were evaporated. The crude product was purified on silica using heptane as eluent to give the title compound (0.96 g, 27% over two steps). 1H NMR (400 MHz, CDCl3) δ ppm 2.44 (d, J=1.20 Hz, 3 H) 3.93 (s, 3 H) 7.03 (ddd, J=8.78, 2.51, 0.50 Hz, 1 H) 7.11 (dq, J=1.20, 0.50 Hz, 1 H) 7.17 (d, J=2.51 Hz, 1 H) 7.73 (dd, J=8.78, 0.50 Hz, 1 H).

1. temperaturewas heated
2. temperatureat reflux over night
3. filtrationThe reaction mixture was filtered
4. customthe solvent was evaporated
5. customgiving 5.0 g crude product
6. temperatureThe reaction mixture was refluxed over night
7. customThe solvent was decanted
8. additionthe PPA residue was treated with CH2Cl2
9. washThe combined organic extracts were washed with water
10. customdried before the solvents
11. customwere evaporated
12. customThe crude product was purified on silica

ORD record

ord-081e76e5d41f4f71861167fb2c71d184

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09233946B2