Reaktion #171396

Reaktionsgleichung

Benzyl alcohol

pyridine

2-Chloropropanoyl chloride

→

title compound

Ausbeute 90.4%

Benzyl 2-chloropropanoate

Ausbeute 90.4%

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe temperature between 0° C. and 5° C
2. 2
   workup.ADDITIONAfter addition the mixture
3. 3
   Temperaturto warm to RT overnight
4. 4
   WaschenThe mixture was washed with 20% aqueous citric acid (2.5 L), saturated aqueous NaHCO3 (2.5 L), brine (2.5 L)
5. 5
   Trocknendried (MgSO4)
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated in vacuo
8. 8
   workup.DISSOLUTIONThe resulting brown liquid (450 g) was dissolved in a small amount of methylene chloride
9. 9
   Filtrationfiltered through a short path of silica gel
10. 10
    EinengenAfter concentration
11. 11
    workup.DISTILLATIONthe crude was purified via bulb-to-bulb distillation (2*10−2 mbar, 90-95° C.)

Vorschrift

Benzyl alcohol (242 mL, 253 g, 2.34 mol) and pyridine (204 mL, 204 g, 2.57 mol) were dissolved in methylene chloride (2.5 L) and cooled to 0° C. 2-Chloropropanoyl chloride (250 mL, 327 g, 2.57 mol) was added dropwise keeping the temperature between 0° C. and 5° C. After addition the mixture was allowed to warm to RT overnight. The mixture was washed with 20% aqueous citric acid (2.5 L), saturated aqueous NaHCO3 (2.5 L), brine (2.5 L), dried (MgSO4), filtered and concentrated in vacuo. The resulting brown liquid (450 g) was dissolved in a small amount of methylene chloride and filtered through a short path of silica gel. After concentration, the crude was purified via bulb-to-bulb distillation (2*10−2 mbar, 90-95° C.) affording the title compound as a pale yellow liquid (420 g, 90%). 1H-NMR: (CDCl3, 300 MHz): δ ppm 1.75 (d, 3H, CH3), 4.45 (q, 1H, CHCl), 5.25 (s, 2H, CH2Ar), 7.40 (m, 5H, ArH).

Quelle