Sodium Cyanide → 13-Hydroxyoctadecanenitrile
Reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([OH:19])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[C-:20]#[N:21].[Na+]>CN(C=O)C.C(OCC)C>[OH:19][CH:13]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:20]#[N:21]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 90 °C
Procedure
To 17-bromoheptadecan-6-ol (1.0 g, 2.98 mmol) in dry DMF, was added NaCN (175 mg, 3.58 mmol) and the resulting reaction mixture heated at 90° C. for 16 hours. After cooling to room temperature, the mixture was diluted with diethyl ether (100 ml), the organic layer was washed with cold water (3×20 ml), brine solution, dried over MgSO4 and concentrated. The crude product was purified over a silica gel column (10% EtOAc in hexane) to give 13-hydroxyoctadecanenitrile as a colorless liquid (0.77 g, 92%).
Workup
- customthe resulting reaction mixture
- temperatureAfter cooling to room temperature
- washthe organic layer was washed with cold water (3×20 ml), brine solution
- dry with materialdried over MgSO4
- concentrationconcentrated
- customThe crude product was purified over a silica gel column (10% EtOAc in hexane)
Sources & evidence
- ORD record
- ord-924e9ceda93b41f7a3a2ac89990b6621
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09365597B2
Reaction notes
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