1,3-Dimethoxybenzene → 1,3-Dimethoxy-2-(4-ethylbenzyl)benzene
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[CH:4]=1.C([Li])CCC.[CH2:16]([C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Br)=[CH:20][CH:19]=1)[CH3:17].[Cl-].[NH4+]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[CH2:22][C:21]1[CH:24]=[CH:25][C:18]([CH2:16][CH3:17])=[CH:19][CH:20]=1Participants
Procedure
To a mixture of 1,3-dimethoxybenzene (6.9 g, 50 mmol) and tetrahydrofuran (70 mL), n-butyllithium (1.57 M in hexane, 35 mL) was added in ice and stirred for 1.5 hours. Subsequently, 4-ethylbenzyl bromide (10 g, 50 mmol) was added in ice and stirred for an additional 3.5 hours. After addition of saturated aqueous ammonium chloride, the reaction mixture was extracted with ethyl acetate, and the organic phase was washed with saturated aqueous sodium chloride and then dried over anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5-85:15) to give 1,3-dimethoxy-2-(4-ethylbenzyl)benzene (6.37 g, 49%, mp 62.5-66.5° C.) as a light-yellow powder.
Workup
- additionwas added in ice
- stirringstirred for an additional 3.5 hours
- extractionthe reaction mixture was extracted with ethyl acetate
- washthe organic phase was washed with saturated aqueous sodium chloride
- dry with materialdried over anhydrous magnesium sulfate
- distillationAfter the solvent was distilled off under reduced pressure
- customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5-85:15)
Sources & evidence
- ORD record
- ord-5d489677f5c5481c960539a4aac2dbdc
- Source dataset
- uspto-grants-2008_08
- Patent number
- US07414072B2
Reaction notes
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