反应详情

温度

25 °C

To magnetically stirred N,N-dimethylformamide (2 ml, 25.8 mmol) cooled in ice was added slowly dropwise thionyl chloride (3 ml, 41.1 mmol), and the resulting cold Vilsmeier reagent was diluted with dichloromethane (10 ml). α-Hydroxy-2-nitrobenzenepropanoic acid (2.00 g, 9.47 mmol), followed by an additional 2 ml of dichloromethane was added. The mixture, protected from moisture, was stirred at room temperature (25° C.) overnight. The resulting solution was evaporated to a syrup. The syrup was dissolved in dichloromethane and the solution was added to stirred ice. The mixture was stirred for 1 hour during which time it warmed to room temperature. The dichloromethane solution was separated and washed (X4) with water and dried (MgSO4). Evaporation gave a syrup which was subjected to an oil pump vacuum for half an hour. The syrup was dissolved in ether and 2,6-dimethylpiperidine was added to approximate neutrality (pH 9 with pH paper). The crude titled product [2.36 g (81%), mp 138°-140° C.] crystallized readily. Recrystallization (methanol-ether) with decolorization (Nuchar C-190N) gave pure product, mp 141°-143° C.

1. additionwas added
2. customThe resulting solution was evaporated to a syrup
3. dissolutionThe syrup was dissolved in dichloromethane
4. additionthe solution was added
5. stirringto stirred ice
6. stirringThe mixture was stirred for 1 hour during which time it
7. temperaturewarmed to room temperature
8. customThe dichloromethane solution was separated
9. washwashed (X4) with water
10. dry with materialdried (MgSO4)
11. customEvaporation
12. customgave a syrup which
13. waitwas subjected to an oil pump vacuum for half an hour
14. customThe crude titled product [2.36 g (81%), mp 138°-140° C.] crystallized readily
15. customRecrystallization (methanol-ether) with decolorization (Nuchar C-190N)
16. customgave pure product, mp 141°-143° C.