Water → 4-tert-Butyl-3-hydroxy-2,6-xylylacetonitrile

HRID 838862Notes

Reaction equation

HRID 838862 reaction equation
[C-:1]#[N:2].[K+].[C:4]([C:8]1[C:13]([OH:14])=[C:12]([CH3:15])[C:11]([CH2:16]Cl)=[C:10]([CH3:18])[CH:9]=1)([CH3:7])([CH3:6])[CH3:5].O>CN(C)C=O>[C:4]([C:8]1[CH:9]=[C:10]([CH3:18])[C:11]([CH2:16][C:1]#[N:2])=[C:12]([CH3:15])[C:13]=1[OH:14])([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 962WaterHCID 9032Potassium Cyanide2×HCID 901316-tert-Butyl-3-(chloromethyl)-2,4-dimethylphenol

Product 1

HCID 1087564-tert-Butyl-3-hydroxy-2,6-xylylacetonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 41 grams of potassium cyanide dispersed in 300 ml of N,N-dimethylformamide, was slowly added a solution of 97.2 grams of the compound of Example 1, the reaction temperature rising from 25° to 35° C. The reaction mixture was then heated at 70° to 75° for 71/2 hours. Since a sample analyzed after 7 hours reaction time indicated that some unreacted starting 6-tert.-butyl-3-chloromethyl-2,4-dimethylphenol remained unreacted, an additional 13.7 grams of potassium cyanide was added and the reaction mixture heated for an additional 2 hours at 60° to 65° C. The reaction mixture was poured on crushed ice, and water added to make the total volume 1.8 liters. The mixture was stirred until the ice melted, the aqueous solid dispersion was filtered by suction, and the filtercake washed well with water. The filtercake was taken up in a toluene-benzene mixture, the resulting solution being successively washed with water, 6N aqueous hydrochloric acid and dried over anhydrous sodium sulfate. After removal of the drying agent by filtration and treating the clear filtrate with activated charcoal, the solvent was evaporated at reduced pressures. The resulting residue was allowed to crystallize from toluene yielding white crystals melting at 134° to 139°.

Workup

  1. customrising from 25° to 35° C
  2. temperatureThe reaction mixture was then heated at 70° to 75° for 71/2 hours
  3. customreaction time
  4. temperaturethe reaction mixture heated for an additional 2 hours at 60° to 65° C
  5. additionThe reaction mixture was poured
  6. additionadded
  7. filtrationthe aqueous solid dispersion was filtered by suction
  8. washthe filtercake washed well with water
  9. washthe resulting solution being successively washed with water, 6N aqueous hydrochloric acid
  10. dry with materialdried over anhydrous sodium sulfate
  11. customAfter removal of the drying agent
  12. filtrationby filtration
  13. additiontreating the clear filtrate with activated charcoal
  14. customthe solvent was evaporated at reduced pressures
  15. customto crystallize from toluene yielding white crystals melting at 134° to 139°

Sources & evidence

ORD record
ord-04fbb75b34f747d9b1643e96b10b3fa9
Source dataset
uspto-grants-1978_06
Patent number
US04093618

Reaction notes

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