Potassium Hydroxide → 6-(But-3-en-1-yloxy)hexanenitrile
Reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]#[N:8].[CH2:9]([OH:13])[CH2:10][CH:11]=[CH2:12].[OH-].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.ClCCl>[CH2:9]([O:13][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]#[N:8])[CH2:10][CH:11]=[CH2:12]Participants
7
Procedure
6-Bromocapronitrile (1.19 ml, 9.00 mmol) and 3-buten-1-ol (946 ul, 11.0 mmol) were added to a stirred solution of potassium hydroxide (6.16 g, 110 mmol) and tetra-butylammonium bromide (434 mg, 1.35 mmol) in water (6 ml) and dichloromethane (2 ml). The reaction was stirred at room temperature for 4 days and then washed with diethyl ether (2×50 ml). The combined organics were washed with water (3×30 ml), dried (magnesium sulphate) and the solvent removed in vacuo to furnish the title compound as a colourless oil, 1.48 g.
Workup
- washwashed with diethyl ether (2×50 ml)
- washThe combined organics were washed with water (3×30 ml)
- dry with materialdried (magnesium sulphate)
- customthe solvent removed in vacuo
Sources & evidence
- ORD record
- ord-98a6237eaba5469894b2f07f624b0954
- Source dataset
- uspto-grants-2009_11
- Patent number
- US07612084B2
Reaction notes
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