Water → HCID 44178882, compound
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[CH2:16](Br)[CH:17]=[CH2:18].O.CN1C(=O)[CH2:25][CH2:24][CH2:23]1>>[CH2:16]([N:1]([C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1)[CH2:25][CH:24]=[CH2:23])[CH:17]=[CH2:18]Participants
6
Conditions
- Temperature
- 80 °C
Procedure
To 3-Aminophenol (10.0 g, 0.092 mol), dissolved, in a flask, in NMP (150 ml), were added 60 ml of triethylamine and 19 ml of allyl bromide. The mixture was stirred under nitrogen at 80° C. Over a 48 hour period, an additional 22 ml of triethyl amine and 9 ml of allyl bromide were added to the flask. After cooling to room temperature, the reaction mixture was poured into 500 ml of distilled water, extracted with diethyl ether, washed with distilled water, dried over magnesium sulfate, filtered and concentrated to yield 13.5 g of 3-(N,N-diallylamino)phenol, as a red oil. Flash chromatography (silica gel, 30:70 THF:hexane) yielded 11.3 g of 3-(N,N-diallylamino)phenol as a pale yellow oil.
Workup
- temperatureAfter cooling to room temperature
- extractionextracted with diethyl ether
- washwashed with distilled water
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-b41b149c145346a3b3a02a612c534f46
- Source dataset
- uspto-grants-1997_09
- Patent number
- US05663308
Reaction notes
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