반응 #2172

반응 방정식

potassium carbonate

Phosphorus oxychloride

DMF

4-chlorophenylacetic acid

→

2-(4-chlorophenyl)-3-dimethylaminopropenal

용매

Toluene

반응 조건

후처리

1. 1
   온도heated to 70°-80° C. during 5.5 hours, during which time the mixture
2. 2
   온도The reaction mixture was cooled
3. 3
   workup.ADDITIONpoured slowly
4. 4
   workup.ADDITIONIce was added intermittently during this addition
5. 5
   온도to maintain the temperature below 15° C
6. 6
   온도the resulting mixture heated at 100° C. for one hour
7. 7
   온도The mixture was cooled
8. 8
   기타The two resulting layers were separated
9. 9
   추출the aqueous layer extracted with toluene (2×100 ml)
10. 10
    세척The combined organic layers were washed with water (5×200 ml)
11. 11
    건조dried over anhydrous sodium sulfate
12. 12
    기타The solvent was evaporated in vacuo
13. 13
    기타the resulting yellow solid was triturated with hexane

실험 절차

Phosphorus oxychloride (92 g) was added dropwise to stirred DMF (78 ml) between 10°-15° C. To the resulting slurry was added 4-chlorophenylacetic acid (34.12 g). The resulting mixture was stirred at room temperature for one half hour and then heated to 70°-80° C. during 5.5 hours, during which time the mixture became effervescent. The reaction mixture was cooled and poured slowly onto cracked ice. The resulting suspension was brought to pH 10 with solid potassium carbonate. Ice was added intermittently during this addition to maintain the temperature below 15° C. Toluene (150 ml) was added and the resulting mixture heated at 100° C. for one hour. The mixture was cooled and allowed to stand overnight. The two resulting layers were separated and the aqueous layer extracted with toluene (2×100 ml). The combined organic layers were washed with water (5×200 ml) and dried over anhydrous sodium sulfate. The solvent was evaporated in vacuo and the resulting yellow solid was triturated with hexane to yield 26 g of 2-(4-chlorophenyl)-3-dimethylaminopropenal as a tan solid mp. 120°-125° C.

출처