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

HRID 1728286Notes

Reaction equation

HRID 1728286 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]

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 6344DichloromethaneSolvent

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-2389d1d0164c45bb9b0646f32866c50e
Source dataset
uspto-grants-1994_07
Patent number
US05326553

Reaction notes

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