반응 #805993

반응 방정식

4-(3-acetamido-4-methylphenyl)-4-oxobutanoic acid

4-(3-Acetamido-4-methylphenyl)-4-oxobutanoic acid

Thionyl chloride

AlCl3

→

N-(3-Methyl-5-oxo-5,6,7,8-tetrahydronaphthalen-2-yl)acetamide

수율 65.0%

용매

nitromethane

반응 조건

후처리

1. 1
   온도maintaining a temperature of about 25° C
2. 2
   workup.STIRRINGThe resulting mixture was stirred for another about 30 min
3. 3
   workup.ADDITIONpoured onto ice water (30 L)
4. 4
   추출The resulting mixture was extracted with EtOAc (1×60 L
5. 5
   세척washed with sat. aq. NaCl (1×10 L), 1 M aq. NaOH (15 L) and sat. aq. NaCl (1×10 L)
6. 6
   건조The organic layer was dried over Na2SO4
7. 7
   여과filtered
8. 8
   농축concentrated

실험 절차

In a mechanically stirred 50 L vessel, 4-(3-acetamido-4-methylphenyl)-4-oxobutanoic acid (74) (675 g, 2.87 mol) was dissolved in nitromethane (13.75 L). Thionyl chloride (255 mL, 3.49 mol) was added. The resulting mixture was stirred for about 1.5 h at rt. AlCl3 (973 g, 7.30 mol) was added maintaining a temperature of about 25° C. The resulting mixture was stirred for another about 30 min and then poured onto ice water (30 L). The resulting mixture was extracted with EtOAc (1×60 L then 2×20 L). The organic layers were combined and washed with sat. aq. NaCl (1×10 L), 1 M aq. NaOH (15 L) and sat. aq. NaCl (1×10 L). The organic layer was dried over Na2SO4, filtered, and concentrated to afford N-(3-Methyl-5-oxo-5,6,7,8-tetrahydronaphthalen-2-yl)acetamide (380 g, 65% yield). 1H NMR (300 MHz, DMSO): δ 9.36 (s, 1H), 7.68 (s, 1H), 7.62 (s, 1H), 2.86 (m, 2H), 2.55 (m, 2H), 2.23 (s, 3H), 2.06 (s, 3H), 2.00 (m, 2H).

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