反応 #3046

反応方程式

2-(1,1-dimethylethyl)-6-methylphenol

hexamethylenetetramine

trifluoroacetic acid

→

desired subtitled intermediate

3-(1,1-dimethylethyl)-4-hydroxy-5-methylbenzaldehyde

反応条件

後処理

1. 1
   温度at reflux temperature for about 24 hours
2. 2
   温度to cool
3. 3
   その他evaporated
4. 4
   その他The residue from the evaporation
5. 5
   その他The resultant layers were separated
6. 6
   洗浄the aqueous layer was washed with chloroform
7. 7
   乾燥The organic layer was dried over sodium sulfate overnight
8. 8
   洗浄after which it was again washed with a volume of chloroform
9. 9
   その他evaporated
10. 10
    温度heated on a steam bath

実験手順

Under a nitrogen atmosphere, 76.65 g of 2-(1,1-dimethylethyl)-6-methylphenol (Aldrich), 65.42 g of hexamethylenetetramine and 700 ml of trifluoroacetic acid were stirred at reflux temperature for about 24 hours, then allowed to cool and evaporated. The residue from the evaporation was taken up in 1500 ml of water and 1000 ml of chloroform and neutralized to pH 7 with solid sodium carbonate. The resultant layers were separated and the aqueous layer was washed with chloroform. The organic layer was dried over sodium sulfate overnight, after which it was again washed with a volume of chloroform and evaporated. The resultant residue was then taken up in 375 ml of toluene, heated on a steam bath and then allowed to cool to room temperature overnight. Subsequent workup gave 28.3 g of the desired subtitled intermediate.

出典