反応 #64369

反応方程式

water

toluquinone

2,3-dimethyl-1,3-butadiene

→

title compound

収率 91.0%

5,8-dihydro-2,6,7-trimethyl-1,4-naphthoquinone

収率 91.0%

溶媒

toluene

acetic acid

反応条件

後処理

1. 1
   workup.STIRRINGstirred further for 3 hours at 40° C
2. 2
   その他The liquid reaction mixture
3. 3
   洗浄was washed with water
4. 4
   その他an organic layer was dried
5. 5
   濃縮concentrated under reduced pressure
6. 6
   workup.ADDITIONConcentrated hydrochloric acid (1 ml) and ethanol (40 ml) were added to the residue
7. 7
   workup.STIRRINGthe mixture was stirred for 1 hour at 40° C
8. 8
   その他After the liquid reaction mixture
9. 9
   濃縮was concentrated under reduced pressure
10. 10
    workup.DISSOLUTIONthe residue was dissolved in a liquid mixture of acetonitrile (70 ml) and water (20 ml)
11. 11
    その他The liquid reaction mixture
12. 12
    抽出extraction with toluene (50 ml × 2)
13. 13
    洗浄The resulting organic layer was washed with water
14. 14
    その他dried
15. 15
    濃縮concentrated under reduced pressure

実験手順

In toluene (30 ml) and acetic acid (10 ml), were dissolved 6.0 g (0.049 mol) of toluquinone, to which 10.0 g (0.12 mol) of 2,3-dimethyl-1,3-butadiene were added at -10° C. under stirring. Thereafter, the resultant mixture was gradually heated and stirred further for 3 hours at 40° C. The liquid reaction mixture was washed with water, and an organic layer was dried and concentrated under reduced pressure. Concentrated hydrochloric acid (1 ml) and ethanol (40 ml) were added to the residue, and the mixture was stirred for 1 hour at 40° C. After the liquid reaction mixture was concentrated under reduced pressure, the residue was dissolved in a liquid mixture of acetonitrile (70 ml) and water (20 ml). To the solution, were added 15.0 g (0.027 mol) of ceric ammonium nitrate at room temperature to stir the resultant mixture for 1 hour. The liquid reaction mixture was poured into water (200 ml) to make extraction with toluene (50 ml × 2). The resulting organic layer was washed with water, dried and concentrated under reduced pressure to obtain 8.9 g of a crude product of the title compound (yield: 91%).

出典