N-(4-PENTANOYL-PHENYL)-ACETAMIDE synthesis
- Product Name:N-(4-PENTANOYL-PHENYL)-ACETAMIDE
- CAS Number:33228-40-9
- Molecular formula:C13H17NO2
- Molecular Weight:219.2796
638-29-9
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Yield:33228-40-9 60%
Reaction Conditions:
with aluminum (III) chloride in carbon disulfide; for 18 h;Heating / reflux;Friedel Crafts Acylation;
Steps:
57
Example 57 N- (4-Pentanoyl-phenyl)-acetamide. Acetanilide (15.0 g, 111 mmol) was taken up in CSz and valeryl chloride (22.5 g, 186 mmol) was added in one portion. AlCl3 (44 g, 330 mmol) was added in 2 g portions to the resulting solution over a period of 0.5 h. The translucent mixture was heated to reflux for 18 h. On cooling, the top layer of CS2 was decanted from the remaining brown oil which was subsequently poured onto ice containing concentrated HC1 (10 mL). The resulting gummy orange solid was collected by filtration, washed with saturated aqueous NaHCO3, then a small volume of Et2O and dried in air. Recrystallization from hot MeOH gave pure N- (4-Pentanoyl-phenyl)-acetamide (14.7 g, 60%) as a colorless solid. 1H NOR 6 7.94 (d, 2H), 7.61 (d, 2H), 7.41 (br, s, 1H), 2.94 (t, 2H), 2.22 (s, 3H), 1.8-1. 65 (m, 2H), 1.45-1. 35 (m, 2H), 0.95 (t, 3H) ; 13C NMR os 168.4, 142.0, 132.9, 129.5, 118.8, 38.2, 26.6, 24. 8, 22.5, 14.0.
References:
WO2005/34878,2005,A2 Location in patent:Page/Page column 44; 45
