تفاعل #64366

معادلة التفاعل

toluquinone

water

1,3-butadiene

lithium chloride

→

title compound

5,8-dihydro-2-methyl 1,4-naphthoquinone

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 toluene (50 ml), n-propanol (25 ml) and water (25 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 (5 ml), were dissolved 7.0 g (0,057 mol) of toluquinone, to which 7.6 g (0.14 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 toluene (50 ml), n-propanol (25 ml) and water (25 ml). To the solution, were added 1.0 g (0.23 mol) of lithium chloride, 5.0 g (0.29 mol) of cupric chloride dihydrate to stir the resultant mixture for 1 hour at 40° C. The liquid reaction mixture was poured into water (100 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 a crude product of the title compound. This crude product was recrystallized from methanol (20 ml) to obtain 9.14 g of the title compound as yellow crystals (yield: 92%).

المصدر