Ammonium Chloride → HCID 19001385, compound

Temperature

25 °C

A solution of 80 mL of 3M methyl magnesium bromide in ether was added to a solution of 32 g of 2-acetyl-5-chlorothiophene in 400 mL of ether at 0° to 10° C. After being stirred for 1 hour at 25° C., the reaction mixture was poured onto saturated aq NH4Cl, washed with brine, dried (MgSO4), and concentrated. The crude carbinol was dissolved in 400 mL of 1-chlorobutane, 0.5 g of potassium hydrogen sulfate was added, and the mixture was heated at reflux with a water separator until the distillate was clear. The reaction mixture was washed with aq. NaHCO3, dried (MgSO4), and concentrated after first adding 0.1 g of 4-t-butyl catechol. Distillation at 90° at aspirator pressure afforded the title compound as a yellow oil. 1H NMR (CDCl3): δ2.08 (s, 3H), 4.95 (s, 1H), 5.25 (s, 1H), 6.77 (s, 2H).

1. washwashed with brine
2. dry with materialdried (MgSO4)
3. concentrationconcentrated
4. dissolutionThe crude carbinol was dissolved in 400 mL of 1-chlorobutane
5. addition0.5 g of potassium hydrogen sulfate was added
6. temperaturethe mixture was heated
7. temperatureat reflux with a water separator until the distillate
8. washThe reaction mixture was washed with aq. NaHCO3
9. dry with materialdried (MgSO4)
10. concentrationconcentrated
11. additionafter first adding 0.1 g of 4-t-butyl catechol
12. distillationDistillation at 90° at aspirator pressure

ORD record

ord-aa63b1d5a5af444a889a17648ecdae62

Source dataset

uspto-grants-1995_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05474998