4-Toluenesulfonyl chloride → 4-Benzyl-2-toluene-p-sulphonyloxymethylmorpholine
Reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([CH2:14][OH:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1>N1C=CC=CC=1>[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([CH2:14][O:15][S:22]([C:19]2[CH:20]=[CH:21][C:16]([CH3:26])=[CH:17][CH:18]=2)(=[O:24])=[O:23])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
To a solution of 4-benzyl-2-hydroxymethylmorpholine (118.8 g.) in dry pyridine (250 ml.) toluene-p-sulphonyl chloride (120.2 g.) is added gradually at 18°-25° C. The mixture is stirred for 20 hours at ambient temperature (ca. 20° C.) and the pyridine is removed under diminished pressure. The residue is diluted with water, the mixture made alkaline by the addition of sodium hydroxide solution, and the product is then extracted into ether. The ethereal solution is dried (MgSO4) and filtered, the ether is evaporated and the residual solid is crystallised from cyclohexane or petroleum ether (b.p. 60°-80° C.) to give 4-benzyl-2-toluene-p-sulphonyloxymethylmorpholine, m.p. 78°-79° C.
Workup
- customthe pyridine is removed under diminished pressure
- additionThe residue is diluted with water
- additionby the addition of sodium hydroxide solution
- extractionthe product is then extracted into ether
- dry with materialThe ethereal solution is dried (MgSO4)
- filtrationfiltered
- customthe ether is evaporated
- customthe residual solid is crystallised from cyclohexane or petroleum ether (b.p. 60°-80° C.)
Sources & evidence
- ORD record
- ord-247e5a4077554e82a1e48da8e91de177
- Source dataset
- uspto-grants-1977_06
- Patent number
- US04029786
Reaction notes
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