Water → 5,8-Dihydro-1,4-naphthoquinone

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%).

1. stirringstirred further for 3 hours at 40° C
2. customThe liquid reaction mixture
3. washwas washed with water
4. customan organic layer was dried
5. concentrationconcentrated under reduced pressure
6. additionConcentrated hydrochloric acid (1 ml) and ethanol (50 ml) were added to the residue
7. stirringthe mixture was stirred for 1 hour at 40° C
8. customAfter the liquid reaction mixture
9. concentrationwas concentrated under reduced pressure
10. dissolutionthe residue was dissolved in a liquid mixture of acetonitrile (100 ml) and water (30 ml)
11. customThe liquid reaction mixture
12. extractionextraction with toluene (50 ml×2)
13. washThe resulting organic layer was washed with water
14. customdried
15. concentrationconcentrated under reduced pressure

ORD 기록

ord-9f0aa4b0444b48ccadbf883fb43e65a9

출처 데이터셋

uspto-grants-1997_03

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US05608092