Water → alpha,2-Dimethyl-5-nitrobenzyl methyl ether
Reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH:11]([OH:13])[CH3:12].[CH3:14]COCC.CI.O>C1C=CC=CC=1.[OH-].[Na+].[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:14][O:13][CH:11]([CH3:12])[C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[CH3:1]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
1-(2'-methyl-5'-nitrophenyl)ethanol (0.9 g) is dissolved in 5 ml of benzene and 0.8 g of 50% aqueous sodium hydroxide, ca 10 mg of tetrabutylammonium chloride, 5 ml of ether and 1.25 ml of methyl iodide is added. The reaction mixture is stirred at room temperature for 2 hours and heated at 30°-35° for 4 hours. An additional 1.0 ml of methyl iodide is added and the mixture stirred at room temperature for 22 hours. Thin layer chromatography indicates starting material remaining therefore 0.52 ml of 50% NaOH solution and 2.0 ml of methyl iodide are added and the mixture stirred at room temperature for 5 days. Water is added and the mixture extracted with ether. The organic layer is washed with water and brine. The solution is evaporated to dryness giving 0.97 g of oil which is purified by column chromatography to give pure material, mp 35°-37° C.
Workup
- temperatureheated at 30°-35° for 4 hours
- stirringthe mixture stirred at room temperature for 22 hours
- stirringthe mixture stirred at room temperature for 5 days
- extractionthe mixture extracted with ether
- washThe organic layer is washed with water and brine
- customThe solution is evaporated to dryness
Sources & evidence
- ORD record
- ord-5ee02cdf721247a2a8ce9aacd86261f5
- Source dataset
- uspto-grants-1981_10
- Patent number
- US04297127
Reaction notes
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