Reaktion #601546

Reaktionsgleichung

acetyl chloride

triethylamine

water

2-(methylsulfanyl)phenol

acetyl chloride

HCl

AlCl3

→

title compound

Ausbeute 37.0%

5-acetyl-2-(methylsulfanyl)phenyl acetate

Ausbeute 37.0%

Lösungsmittel

CS2

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction mixture was heated under reflux conditions for 3 h
2. 2
   workup.ADDITIONwas added
3. 3
   Extraktionthe reaction mixture was extracted with CH2Cl2
4. 4
   WaschenThe combined organic layers were washed with brine
5. 5
   Trocknendried over Na2SO4
6. 6
   Einengenconcentrated
7. 7
   workup.DISSOLUTIONThe residue was dissolved in CH2Cl2 (50 mL)
8. 8
   Temperaturcooled to 0° C.
9. 9
   workup.STIRRINGThe mixture was stirred at rt for 2 h
10. 10
    SonstigeAfter separation of the layers
11. 11
    Waschenthe organic phase was washed successively with water, 3 N HCl and 10% aq. KHCO3
12. 12
    Trocknendried over Na2SO4
13. 13
    Sonstigeevaporated to dryness
14. 14
    SonstigeRecrystallization of the resulting solid from benzene-hexane

Vorschrift

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).

Quelle