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(+-)-2-Undecanol → 2-Methanesulfonyloxyundecane

HRID 53485
Notes
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Reaction equation

HRID 53485 reaction equation
[CH3:1][S:2]([O:5][CH:6]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH3:7])(=[O:4])=[O:3].[CH3:16]C(O)CCCCCCCCC.CS(Cl)(=O)=O.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH3:1][S:2]([O:5][CH:6]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH3:7])(=[O:4])=[O:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 15448(+-)-2-UndecanolHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 14916009Decan-2-yl methanesulfonate

Product 1

HCID 153433162-MethanesulfonyloxyundecaneYield 95%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

2-Methanesulfonyloxyundecane was prepared as described for 2-methanesulfonyloxydecane from 2-undecanol (30.0 ml, 144 mmol), methanesulfonylchloride (15.5 ml, 200 mmol) and diisopropylethylamine (30.8 ml, 177 mmol) in dry CH2Cl2 (240 ml). After stirring for 3.5 hrs, the reaction was processed as previously stated but at 4 times the volumes to provide 2-methanesulfonyloxyundecane (31.35 g, 95%).

Workup

  1. custom2-Methanesulfonyloxyundecane was prepared

Sources & evidence

ORD record
ord-5a81bd2a8d654ff5a9d31876ec213083
Source dataset
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05620677

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes