Chloroacetone → HCID 14343474, compound

Temperature

100 °C

A mixture of 2-methoxylthiophenol (915 mg, 6.5 mmol), chloroacetone (1.1 mL, 13.8 mmol) and K2CO3 (1.8 g, 13 mmol) in acetone (15 mL) was refluxed for 2 h. The mixture was filtered and the solvent evaporated. The crude product was dissolved in chlorobenzene (30 mL) and polyphosphoric acid (PPA, 0.5 g) was added (Plé et al., (1988) J. Heterocyclic Chem. 25, 1271-1272). The resulting mixture was heated at 100° C. over night, and then refluxed for 5 h. The solvent was decanted from the PPA-residue. The residue was then treated with CH2Cl2 and 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 (620 mg, 53% yield over two steps). 1H NMR (400 MHz, CDCl3) δ ppm 2.43 (d, J=1.13 Hz, 3 H) 4.01 (s, 3 H) 6.77-6.83 (m, 1 H) 7.06 (qd, J=1.17, 0.53 Hz, 1 H) 7.32-7.39 (m, 2 H).

1. temperaturewas refluxed for 2 h
2. filtrationThe mixture was filtered
3. customthe solvent evaporated
4. dissolutionThe crude product was dissolved in chlorobenzene (30 mL)
5. additionpolyphosphoric acid (PPA, 0.5 g) was added (Plé et al., (1988) J. Heterocyclic Chem. 25, 1271-1272)
6. temperaturerefluxed for 5 h
7. customThe solvent was decanted from the PPA-residue
8. additionThe residue was then 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-683376e02d094238b535e36564e3aeca

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09233946B2