Sodium Hydroxide → 3-(Hexyloxy)-6-hydroxybenzene-1,2-dicarbonitrile

HRID 892382

반응식

HRID 892382 반응식
[C:1]1(C)[CH:6]=[CH:5][C:4](S(OCCCCCC)(=O)=O)=[CH:3][CH:2]=1.[C:18]([C:20]1[C:21]([C:28]#[N:29])=[C:22]([CH:24]=[CH:25][C:26]=1[OH:27])[OH:23])#[N:19].[OH-].[Na+]>>[CH2:5]([O:27][C:26]1[CH:25]=[CH:24][C:22]([OH:23])=[C:21]([C:28]#[N:29])[C:20]=1[C:18]#[N:19])[CH2:6][CH2:1][CH2:2][CH2:3][CH3:4]

참가 물질

4

반응물 3

HCID 14798Sodium HydroxideHCID 784672,3-DicyanohydroquinoneHCID 220448Hexyl p-Toluenesulfonate

생성물 1

HCID 150066893-(Hexyloxy)-6-hydroxybenzene-1,2-dicarbonitrile수율 27.5%

실험 절차

11.3 g (44.1 mM) of n-hexyl p-toluenesulfonate was added to the mixture of 5.0 g (31.3 mM) of dicyanohydroquinone and 37.5 ml of 5% NaOH aqueous solution, followed by 7 hours of stirring under refluxing. After the reaction, the reaction mixture was washed with toluene and the aqueous layer was acidified with HCl. The resultant precipitate was recovered through filtration and dried. To the precipitate, 1 liter of toluene was added. After the insoluble substrate was filtered out, the filtrate was subjected to recrystallization in a refrigerator and further subjected to recrystallization from a mixture solvent of water/methanol to obtain 2.1 g of an objective product (yield: 27.5%). m.p.: 150°-153° C.

후처리

  1. temperatureunder refluxing
  2. customAfter the reaction
  3. washthe reaction mixture was washed with toluene
  4. filtrationThe resultant precipitate was recovered through filtration
  5. customdried
  6. additionTo the precipitate, 1 liter of toluene was added
  7. filtrationAfter the insoluble substrate was filtered out
  8. customthe filtrate was subjected to recrystallization in a refrigerator
  9. customfurther subjected to recrystallization from a mixture solvent of water/methanol

출처 및 근거

ORD 기록
ord-530bb1a0d7914875b4dc65c98f76c6ee
출처 데이터셋
uspto-grants-1992_06
특허 번호
US05118441

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