Water → 5,8-Dihydro-2-methyl 1,4-naphthoquinone

HRID 975478

반응식

HRID 975478 반응식
[C:1]1([CH3:9])[C:2](=O)[C:3](=[O:7])[CH:4]=[CH:5][CH:6]=1.[CH2:10]=[CH:11][CH:12]=[CH2:13].[Cl-].[Li+].[OH2:16]>C1(C)C=CC=CC=1.C(O)(=O)C>[CH3:9][C:1]1[C:6](=[O:16])[C:5]2[CH2:10][CH:11]=[CH:12][CH2:13][C:4]=2[C:3](=[O:7])[CH:2]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 78451,3-ButadieneHCID 433294Lithium ChlorideHCID 123257543-Methylcyclohexa-3,5-diene-1,2-dione

생성물 1

HCID 190786525,8-Dihydro-2-methyl 1,4-naphthoquinone

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 1140Toluene용매

실험 절차

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%).

후처리

  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 toluene (50 ml), n-propanol (25 ml) and water (25 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

출처 및 근거

ORD 기록
ord-0fca03055895448b9f5f927949ac94b5
출처 데이터셋
uspto-grants-1997_03
특허 번호
US05608092

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