2-Methoxybenzaldehyde → (2-Methoxyphenyl)(3-methyl-2-methoxymethoxyphenyl)methanol
Reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:9][O:10][CH3:11].C([Li])CCC.[CH:17](=[O:26])[C:18]1[C:19]([O:24][CH3:25])=[CH:20][CH:21]=[CH:22][CH:23]=1.[Cl-].[NH4+]>CCCCCC.CN(C)CCN(C)C.O1CCCC1>[CH3:25][O:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[CH:17]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=1[O:8][CH2:9][O:10][CH3:11])[OH:26]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
1-Methyl-2-methoxymethoxybenzene (15.2 g) was added to a mixture of 75 ml of a 1.6M solution of n-butyl lithium in hexane and 18.1 ml of tetramethylethylenediamine at 0° C. with stirring. After 4 hours, 13.6 g of o-anisaldehyde dissolved in 30 ml of tetrahydrofuran was added. The mixture was allowed to react for 0.5 hour and was then poured into a mixture of ice and saturated aqueous ammonium chloride. The resulting mixture was extracted with ether and the ether extract was dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure to obtain 39.5 g of the title compound as an off-white solid. The assigned structure was consistent with the proton NMR spectrum.
Workup
- additionwas added
- customto react for 0.5 hour
- extractionThe resulting mixture was extracted with ether
- extractionthe ether extract
- dry with materialwas dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated by evaporation under reduced pressure
Sources & evidence
- ORD record
- ord-1716fa5e85214cb28145536063e69974
- Source dataset
- uspto-grants-1992_10
- Patent number
- US05158597
Reaction notes
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