Chloromethyl Methyl Ether → N-ethyl-N-[2-(methoxymethyl)oxyethyl]aniline
Reaction equation
[CH2:1]([N:3]([CH2:10][CH2:11][OH:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2].CCCCCC.[CH3:19][O:20][CH2:21]Cl>O1CCCC1>[CH2:1]([N:3]([CH2:10][CH2:11][O:12][CH2:19][O:20][CH3:21])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
55.7 g (0.34 mol) of N-ethyl-N-(2-hydroxylethyl)aniline was dissolved in 250 ml of anhydrous tetrahydrofuran, and 162 ml (1.2-fold equivalent weight) of a 2.5M hexane solution n-butyllithium was dropwise added thereto over a period of 30 minutes at 0° C. in an atmosphere of argon, followed by stirring at 0° C. for 30 minutes. Next, to the reaction solution obtained, 30.0 g (1.09-fold equivalent weight) of methoxymethyl chloride was dropwise added, and the solution was heated and refluxed for 12 hours, followed by cooling. The precipitate formed was removed by filtration, and thereafter the filtrate obtained was concentrated under reduced pressure. The oily residue thus obtained was distilled under reduced pressure to obtain 63 g of N-ethyl-N-[2-(methoxymethyl)oxyethyl]aniline (yield: 89%).
Workup
- customNext, to the reaction solution obtained
- temperaturethe solution was heated
- temperaturerefluxed for 12 hours
- temperatureby cooling
- customThe precipitate formed
- customwas removed by filtration
- customthe filtrate obtained
- concentrationwas concentrated under reduced pressure
- customThe oily residue thus obtained
- distillationwas distilled under reduced pressure
Sources & evidence
- ORD record
- ord-ace98e2e886e4639a8b04a97b855a07a
- Source dataset
- uspto-grants-1998_11
- Patent number
- US05834575
Reaction notes
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