p-Toluenesulfonic acid monohydrate → 2-Acetyl-4-allyloxycarbonylmorpholine

HRID 1029667Notes

Reaction equation

HRID 1029667 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][O:10][CH:9]([C:13]2([CH3:18])OCC[O:14]2)[CH2:8]1)=[O:6])[CH:2]=[CH2:3].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[C:13]([CH:9]1[O:10][CH2:11][CH2:12][N:7]([C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:6])[CH2:8]1)(=[O:14])[CH3:18]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 151173044-Allyloxycarbonyl-2-(2-methyl-1,3-dioxolan-2-yl)morpholine

Product 1

HCID 151173052-Acetyl-4-allyloxycarbonylmorpholineYield 75.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 4-allyloxycarbonyl-2-[2-methyl-1,3-dioxolan-2-yl)morpholine (2.20 g) in acetone (22 ml) was stirred at ambient temperature for 5 days in the presence of p-toluenesulfonic acid monohydrate (1.10 g). The mixture was concentrated under reduced pressure to give a syrup. The syrup was subjected to a column chromatography on silica gel (25 g) and eluted with a mixture of hexane and ethyl acetate (9:1, V/V) to give 2-acetyl-4-allyloxycarbonylmorpholine (1.37 g) as a syrup.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customto give a syrup
  3. washeluted with a mixture of hexane and ethyl acetate (9:1, V/V)

Sources & evidence

ORD record
ord-03358dd3dd254cc48218e5ab3dcc380a
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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