Water → 16-Cyanohexadecanoic acid
Reaction equation
C1(C)C=CC(S(O[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])(=O)=O)=CC=1.[C-:30]#[N:31].[Na+].C(OCC)C.O>CS(C)=O>[C:30]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])#[N:31]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
The methyl ester of 16-paratoluenesulfonyloxy-hexadecanoic acid (600 mg) was dissolved in dimethylsulfoxide (DMSO). Sodium cyanide (250 mg) was added to the solution, and the mixture was stirred at 80° C. for 5 hours. After the reaction mixture was cooled, it was distributed into diethyl ether and water. The diethyl ether layer is dried over anhydrous sodium sulfate and concentrated to give the methyl ester of 16-cyanohexadecanoic acid (370 mg). The product was dissolved in a mixed solvent of ethanol-water (1:1), and lithium hydroxide (180 mg) was added to the solution. The mixture was stirred at 80° C. for 30 minutes. The reaction mixture was cooled and ethanol was removed by distillation and extracted with ethyl acetate which had been adjusted to a weak acidic range of pH by adding citric acid. The ethyl acetate layer was dried and concentrated to give 16-cyanohexadecanoic acid (316 mg).
Workup
- temperatureAfter the reaction mixture was cooled
- dry with materialThe diethyl ether layer is dried over anhydrous sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-6c84b7c083794689a9967432c7600d3b
- Source dataset
- uspto-grants-1997_05
- Patent number
- US05631238
Reaction notes
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