반응 #3047

반응 방정식

N-methylformanilide

phosphoryl chloride

ortho-t-butylphenol

→

desired subtitled intermediate

수율 22.6%

3-(1,1-dimethylethyl)-4-hydroxybenzaldehyde

수율 22.6%

반응 조건

후처리

1. 1
   workup.STIRRINGstirred for about 45 minutes after which the mixture
2. 2
   온도was heated to about 50°-60° C.
3. 3
   workup.STIRRINGto stir for 4.5 hours
4. 4
   workup.ADDITIONThe reaction mixture was poured into a volume of crushed ice
5. 5
   추출extracted with chloroform
6. 6
   기타The aqueous layer was separated
7. 7
   세척washed again with chloroform
8. 8
   추출extracted with 2000 ml of a 5% potassium hydroxide solution
9. 9
   기타The aqueous potassium hydroxide layer was separated
10. 10
    workup.ADDITIONadded to 1000 ml of chloroform
11. 11
    workup.STIRRINGwith stirring
12. 12
    기타The resultant layers were separated
13. 13
    추출the aqueous layer was again extracted with chloroform
14. 14
    건조dried over sodium sulfate overnight

실험 절차

Into 101.5 g of N-methylformanilide was added dropwise with cooling 107 g of phosphoryl chloride over a period of 15 minutes. The mixture was allowed to warm to room temperature and stirred for 70 minutes. 67.5 g of ortho-t-butylphenol was added and stirred for about 45 minutes after which the mixture was heated to about 50°-60° C. and allowed to stir for 4.5 hours. The reaction mixture was poured into a volume of crushed ice and extracted with chloroform. The aqueous layer was separated and washed again with chloroform. The chloroform layers were combined and extracted with 2000 ml of a 5% potassium hydroxide solution. The aqueous potassium hydroxide layer was separated and added to 1000 ml of chloroform. The pH of the resulting two-phase mixture was adjusted to 3 with concentrated hydrochloric acid with stirring. The resultant layers were separated and the aqueous layer was again extracted with chloroform and dried over sodium sulfate overnight to give 18.1 g of the desired subtitled intermediate.

출처