Reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][CH:13]=[CH:12][C:4]=1[CH:5]=[CH:6][C:7](OCC)=[O:8].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+].[H-]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:15]=[CH:14][CH:13]=[CH:12][C:4]=1[CH2:5][CH2:6][CH2:7][OH:8]Participants
Procedure
A solution of 980 mg of ethyl 2-methoxycinnamate in 15 ml of tetrahydrofuran was added dropwise to a dispersion of 290 mg of lithium aluminum hydride and 10 ml of tetrahydrofuran, whilst ice-cooling. After the addition was complete, the reaction mixture was stirred at room temperature for 1.5 hours, and then sufficient sodium sulfate decahydrate was slowly added, whilst ice-cooling, to the mixture in order to decompose any excess of the hydride. Insoluble materials were filtered off, and the filtrate was concentrated by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a 3:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 640 mg of 3-(2-methoxyphenyl)propanol as a colorless oil.
Workup
- temperaturecooling
- additionAfter the addition
- temperaturecooling, to the mixture in order
- filtrationInsoluble materials were filtered off
- concentrationthe filtrate was concentrated by distillation under reduced pressure
- customThe resulting residue was purified by column chromatography through silica gel
- additionby volume mixture of hexane and ethyl acetate as the eluent
Sources & evidence
- ORD record
- ord-88cc5d468bbc4a44826ea7d8588e3aeb
- Source dataset
- uspto-grants-1996_09
- Patent number
- US05556864
Linked notes
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