تفاعل #64367

معادلة التفاعل

water

1,4-benzoquinone

1,3-butadiene

→

title compound

المردود 91.0%

5,8-dihydro-1,4-naphthoquinone

المردود 91.0%

المذيبات

toluene

acetic acid

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGstirred further for 3 hours at 40° C
2. 2
   أخرىThe liquid reaction mixture
3. 3
   غسيلwas washed with water
4. 4
   أخرىan organic layer was dried
5. 5
   تركيزconcentrated under reduced pressure
6. 6
   workup.ADDITIONConcentrated hydrochloric acid (1 ml) and ethanol (50 ml) were added to the residue
7. 7
   workup.STIRRINGthe mixture was stirred for 1 hour at 40° C
8. 8
   أخرىAfter the liquid reaction mixture
9. 9
   تركيزwas concentrated under reduced pressure
10. 10
    workup.DISSOLUTIONthe residue was dissolved in a liquid mixture of acetonitrile (100 ml) and water (30 ml)
11. 11
    أخرىThe liquid reaction mixture
12. 12
    استخلاصextraction with toluene (50 ml × 2)
13. 13
    غسيلThe resulting organic layer was washed with water
14. 14
    أخرىdried
15. 15
    تركيزconcentrated under reduced pressure

الإجراء التجريبي

In toluene (30 ml) and acetic acid (10 ml), were dissolved 10.0 g (0.092 mol) of 1,4-benzoquinone, to which 10.0 g (0.18 mol) of 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 (50 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 (100 ml) and water (30 ml). To the solution, were added 20.0 g (0.036 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 13.3 g of a crude product of the title compound (yield: 91%).

المصدر