反応 #3047

反応方程式

N-methylformanilide

phosphoryl chloride

ortho-t-butylphenol

→

desired subtitled intermediate

収率 22.6%

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

収率 22.6%

反応条件

後処理

1. 1
   workup.STIRRINGstirred for about 45 minutes after which the mixture
2. 2
   温度was 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
   抽出extracted with chloroform
6. 6
   その他The aqueous layer was separated
7. 7
   洗浄washed again with chloroform
8. 8
   抽出extracted with 2000 ml of a 5% potassium hydroxide solution
9. 9
   その他The aqueous potassium hydroxide layer was separated
10. 10
    workup.ADDITIONadded to 1000 ml of chloroform
11. 11
    workup.STIRRINGwith stirring
12. 12
    その他The resultant layers were separated
13. 13
    抽出the aqueous layer was again extracted with chloroform
14. 14
    乾燥dried over sodium sulfate overnight

実験手順

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.

出典