Water → Benzeneacetonitrile, 4-(2,2-dimethyl-1-oxopropyl)-
Reaction equation
[C-:1]#[N:2].[Na+].O.Br[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:9][CH:8]=1>C(O)C>[C:13]([C:10]1[CH:11]=[CH:12][C:7]([CH2:6][C:1]#[N:2])=[CH:8][CH:9]=1)(=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
A solution of 34.3 g. (0.700 mole) sodium cyanide in 40 ml. of water is warmed to 50°C. and a solution of α-bromo-4-pivaloyl toluene in 85 ml. ethanol is then added dropwise at such a rate as to maintain the temperature at 50°C. After the addition is complete, the mixture is refluxed for four hours. The excess ethanol is removed in vacuo and the resulting residue is treated with ether/water. The layers are separated and the ether is washed with cold 50% sulfuric acid, water and sodium bicarbonate; then the ether layer is dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo. The residue is distilled in vacuo to give 4-pivaloylphenyl acetonitrile (b.p. 143°-148°C/0.75 mm n22 =1.5244.)
Workup
- additionAfter the addition
- temperaturethe mixture is refluxed for four hours
- customThe excess ethanol is removed in vacuo
- additionthe resulting residue is treated with ether/water
- customThe layers are separated
- washthe ether is washed with cold 50% sulfuric acid, water and sodium bicarbonate
- dry with materialthen the ether layer is dried over anhydrous magnesium sulfate
- filtrationfiltered
- customevaporated in vacuo
- distillationThe residue is distilled in vacuo
Sources & evidence
- ORD record
- ord-13536c7b300b43629ac64e1ccf95e851
- Source dataset
- uspto-grants-1976_06
- Patent number
- US03962342
Reaction notes
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