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

HRID 892382

Reaction equation

HRID 892382 reaction equation
[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]

Participants

4

Reactant 3

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

Product 1

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

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-530bb1a0d7914875b4dc65c98f76c6ee
Source dataset
uspto-grants-1992_06
Patent number
US05118441

Linked notes

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