Aniline → 1-(Phenylamino)butan-2-ol

HRID 4121

Reaction equation

HRID 4121 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]=1

Participants

7

Reactant 4

HCID 6115AnilineHCID 78341,2-EpoxybutaneHCID 312751,4-DioxaneHCID 522689Potassium Fluoride

Product 1

HCID 140721971-(Phenylamino)butan-2-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

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

  1. temperatureThe mixture heated
  2. temperatureto reflux for 30 hours
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe residue was distilled under vacuum

Sources & evidence

ORD record
ord-81dc0c6c46c04f688c9e0a0ed9716418
Source dataset
uspto-grants-1988_02
Patent number
US04723986

Linked notes

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