Aniline → 1-(Phenylamino)butan-2-ol
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCOCC1.[O:14]1[CH:16]([CH2:17][CH3:18])[CH2:15]1.[F-].[K+]>O.C(Cl)Cl>[C:2]1([NH:1][CH2:15][CH:16]([OH:14])[CH2:17][CH3:18])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
Aniline, (102.3 g, 1.1 mole) was added to 50 ml of dioxane, 108 g of 1,2-epoxy butane and 1 g of potassium fluoride in 25 ml of water. The mixture heated to reflux for 30 hours. The mixture was poured into water, taken up in 200 ml of methylene chloride, dried over anhydrous magnesium sulfate and stripped under vacuum. The residue was distilled under vacuum and the product, b.p. 98°-106° C. at 0.15 mm, weighed 94 g and was 97% pure by GLPC. It was characterized by IR and NMR.
Workup
- temperatureThe mixture heated
- temperatureto reflux for 30 hours
- dry with materialdried over anhydrous magnesium sulfate
- distillationThe residue was distilled under vacuum
Sources & evidence
- ORD record
- ord-81dc0c6c46c04f688c9e0a0ed9716418
- Source dataset
- uspto-grants-1988_02
- Patent number
- US04723986
Reaction notes
Loading…