N,N,N',N'-Tetramethylethylenediamine → (2-Methoxymethoxyphenyl)(2-hydroxy-3-methoxyphenyl)methanol
Reaction equation
C([Li])CCC.CN(C)CCN(C)C.[CH3:14][O:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[OH:24][C:25]1[C:32]([O:33][CH3:34])=[CH:31][CH:30]=[CH:29][C:26]=1[CH:27]=[O:28].[Cl-].[NH4+]>CCOCC>[CH3:14][O:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH:27]([C:26]1[CH:29]=[CH:30][CH:31]=[C:32]([O:33][CH3:34])[C:25]=1[OH:24])[OH:28]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A 1.6 M solution of butyl lithium (90.6 ml, 0.145 mol) was placed in a flask and blanketed with nitrogen and to this was added with stirring, while maintaining the temperature at 25°-30° C., 16.85 g, (0.145 mol) of tetramethylethylenediamine. The mixture was then cooled to 0° C. and 20.0 g (0.145 mol) of methoxymethoxybenzene was added with stirring and allowed to react for 2 hours after which 10.0 g (0.066 mol) of 2-hydroxy-3-methoxybenzaldehyde was added under the same conditions. The mixture was allowed to react for a few minutes and was then poured into a mixture of ice and saturated aqueous ammonium chloride. The solid that formed, which was insoluble in ether, was collected by filtration to obtain 15.5 g (81 percent of theory) of the title compound. The proton nmr spectrum was consistent with the assigned structure.
Workup
- additionto this was added
- temperaturewhile maintaining the temperature at 25°-30° C.
- stirringwith stirring
- additionwas added under the same conditions
- customto react for a few minutes
- customThe solid that formed
- filtrationwas collected by filtration
Sources & evidence
- ORD record
- ord-fe29d7dee63d4ffaaee0417b8a7c3add
- Source dataset
- uspto-grants-1990_12
- Patent number
- US04979978
Reaction notes
Loading…