Hydrochloric Acid → 5-Acetyl-2-(methylsulfanyl)phenyl acetate

To a solution of 2-(methylsulfanyl)phenol (4.2 g, 30 mmol) in CS2 (50 mL) was added dropwise acetyl chloride (5.2 g, 66 mmol) at 0° C. for 10 min. The resulting mixture was stirred for 20 min at rt. Then AlCl3 (10.8 g, 81 mmol) was added, and the reaction mixture was heated under reflux conditions for 3 h. The reaction mixture was poured into ice water, conc. HCl (5 mL) was added, and the reaction mixture was extracted with CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The residue was dissolved in CH2Cl2 (50 mL), cooled to 0° C. and treated successively with acetyl chloride (1.2 g, 15 mmol) and triethylamine (1.5 g, 15 mmol). The mixture was stirred at rt for 2 h and poured into water. After separation of the layers, the organic phase was washed successively with water, 3 N HCl and 10% aq. KHCO3, dried over Na2SO4, and evaporated to dryness. Recrystallization of the resulting solid from benzene-hexane afforded the title compound (2.5 g, 37%). 1H NMR (400 MHz, CDCl3): δ 2.08 (3H, s), 2.47 (3H, s), 2.55 (3H, s), 7.26 (1H, d, J=4.8 Hz), 7.57 (1H, d, J=4.8 Hz), 7.60 (1H, s).

1. temperaturethe reaction mixture was heated under reflux conditions for 3 h
2. additionwas added
3. extractionthe reaction mixture was extracted with CH2Cl2
4. washThe combined organic layers were washed with brine
5. dry with materialdried over Na2SO4
6. concentrationconcentrated
7. dissolutionThe residue was dissolved in CH2Cl2 (50 mL)
8. temperaturecooled to 0° C.
9. stirringThe mixture was stirred at rt for 2 h
10. customAfter separation of the layers
11. washthe organic phase was washed successively with water, 3 N HCl and 10% aq. KHCO3
12. dry with materialdried over Na2SO4
13. customevaporated to dryness
14. customRecrystallization of the resulting solid from benzene-hexane

ORD-Eintrag

ord-41ef2f427b0a480f84b86f7a5b88b40a

Quelldatensatz

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08987461B2