Ethanol → HCID 20038865, compound

HRID 1904316Notes

Reaction equation

HRID 1904316 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH3:11])[C:9]=1[OH:10])[CH:5]=O.C(O)C.[C-:15]#[N:16].[K+].[CH3:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:20]=1[OH:26]>S(=O)(=O)(O)O.O>[OH:10][C:9]1[C:2]([CH3:1])=[CH:3][C:4]([CH:5]([C:23]2[CH:22]=[C:21]([CH3:25])[C:20]([OH:26])=[C:19]([CH3:18])[CH:24]=2)[C:15]#[N:16])=[CH:7][C:8]=1[CH3:11]

Participants

7

Reactant 4

HCID 702EthanolHCID 9032Potassium CyanideHCID 113352,6-DimethylphenolHCID 752223,5-Dimethyl-4-hydroxybenzaldehyde

Product 1

HCID 20038865HCID 20038865, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

Five grams of 3,5-dimethyl-4-hydroxybenzaldehyde is suspended with stirring in 20 ml of 50% by volume aqueous ethanol. 2.6 gm of potassium cyanide is added in one addition. After one hour, a freshly prepared solution of 6 gm 2,6-dimethylphenol in 10 ml of concentrated sulfuric acid is added slowly over a period of about one minute. An exothermic reaction takes place. After stirring for one hour, the mixture is poured into 100 ml of water. A brown solid containing the named product is filtered off and washed with water. It is dissolved in 10 ml tetrahydrofuran and stirred vigorously for several hours with a solution of 10 gm sodium bisulfite in 50 ml of water. The product is subsequently extracted with ether, washed with brine, dried with magnesium sulfate, filtered and concentrated to yield 5.81 grams of the title compound, a yellow solid.

Workup

  1. customAn exothermic reaction
  2. additionA brown solid containing the named product
  3. filtrationis filtered off
  4. washwashed with water
  5. dissolutionIt is dissolved in 10 ml tetrahydrofuran
  6. stirringstirred vigorously for several hours with a solution of 10 gm sodium bisulfite in 50 ml of water
  7. extractionThe product is subsequently extracted with ether
  8. washwashed with brine
  9. dry with materialdried with magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-1638c72289c64a7abb7c232d47ac8d37
Source dataset
uspto-grants-1989_06
Patent number
US04837293

Reaction notes

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