3-Hydroxybenzyl alcohol → Benzenemethanol, 3-(2-quinolinylmethoxy)-
Reaction equation
[H-].[Na+].[OH:3][CH2:4][C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1.Cl[CH2:13][C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=1.[Cl-].[NH4+]>CCCCCC.O1CCCC1.CN(C)C=O>[N:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:22]=[CH:23][C:14]=1[CH2:13][O:11][C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=1)[CH2:4][OH:3]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
60% Sodium hydride dispersion in oil (0.70 g, 17.5 mmol) was washed with hexane under nitrogen and suspended in dry tetrahydrofuran (30 ml). A solution of 3-hydroxymethylphenol (2.14 g, 17.2 mmol) in dry dimethylformamide was added dropwise to the stirred suspension at 5°-10° C. and the mixture was stirred for 30 minutes at room temperature. A solution of 2-chloromethylquinoline (3.07 g, 17.2 mmol) in tetrahydrofuran (10 ml) was added dropwise and the mixture was stirred for 22 hours at room temperature and 7 hours at 40° C. then poured onto saturated ammonium chloride solution (100 ml) and extracted with dichloromethane. The extract was washed with water, dried and evaporated to a viscous oil which crystallised from ethyl acetate-hexane, m.p. 70° C.
Workup
- stirringthe mixture was stirred for 22 hours at room temperature and 7 hours at 40° C.
- extractionextracted with dichloromethane
- washThe extract was washed with water
- customdried
- customevaporated to a viscous oil which
- customcrystallised from ethyl acetate-hexane, m.p. 70° C.
Sources & evidence
- ORD record
- ord-8a3e03be69404c7184beeb53bad232dd
- Source dataset
- uspto-grants-1994_01
- Patent number
- US05281593
Reaction notes
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