Hydrochloric Acid → 1-Ethynyl-4-(6-methoxyhexyloxy)benzene
Reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]#[C:17]C(C)(O)C)=[CH:12][CH:11]=1.[H-].[Na+].C(OC(C)C)(C)C.Cl>C1(C)C=CC=CC=1.O>[C:16]([C:13]1[CH:14]=[CH:15][C:10]([O:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1])=[CH:11][CH:12]=1)#[CH:17]Participants
7
Procedure
Under a nitrogen atmosphere, to a solution of 4-[4-(6-methoxyhexyloxy)phenyl]-2-methyl-3-butyn-2-ol (3.0 g) in toluene (18 ml) was added sodium hydride (abt. 60% in oil suspension), and the mixture was refluxed for 2 hours. After cooling, to the reaction mixture was added isopropyl ether (100 ml) and water (100 ml), and neutralized by 1N-hydrochloric acid. The organic layer was separated, washed with water and brine, dried over magnesium sulfate. Magnesium sulfate was filtered off, and the filtrate was evaporated under reduced pressure to give a crude red oil. The crude red oil was purified by silica gel chromatography (10:1 hexane-ethyl acetate) to give 1-ethynyl-4-(6-methoxyhexyloxy)benzene (2.39 g) as an orange powder.
Workup
- temperaturethe mixture was refluxed for 2 hours
- temperatureAfter cooling, to the reaction mixture
- customThe organic layer was separated
- washwashed with water and brine
- dry with materialdried over magnesium sulfate
- filtrationMagnesium sulfate was filtered off
- customthe filtrate was evaporated under reduced pressure
- customto give a crude red oil
- customThe crude red oil was purified by silica gel chromatography (10:1 hexane-ethyl acetate)
Sources & evidence
- ORD record
- ord-61d422cfea9547d0aee7c64cf83b33fb
- Source dataset
- uspto-grants-2005_04
- Patent number
- US06884868B1
Reaction notes
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