Ethanol → Linoleyl methanesulfonate

HRID 2205269Notes

Reaction equation

HRID 2205269 reaction equation
[CH2:1]([OH:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C(N(CC)CC)C.[CH3:27][S:28](Cl)(=[O:30])=[O:29].C(O)C>P(=O)(O)(O)O.S([O-])([O-])(=O)=O.[Cu+2].C(Cl)(Cl)Cl.C1(C)C=CC=CC=1>[CH3:27][S:28]([O:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])(=[O:30])=[O:29]

Participants

8

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 5365682Linoleyl alcohol2×

Product 1

HCID 59753235Linoleyl methanesulfonateYield 93%

Reagents, catalysts & solvents 3

HCID 131735811HCID 131735811, compoundCatalystHCID 1140TolueneSolventHCID 6212ChloroformSolvent

Conditions

Temperature
10 °C

Procedure

Dehydrated toluene (500 g), linoleyl alcohol (cis,cis-9,12-octadecadiene-1-ol, 100 g, 375 mmol), and triethylamine (46 g, 450 mmol) were added to a four-necked flask, and agitation was performed in a nitrogen atmosphere. After cooling to 10° C., methanesulfonyl chloride (47 g, 413 mmol) was dropped over 2 hours in such a way that the reaction temperature became 30° C. or lower. One hour from completion of dropping, the reaction solution was sampled, and disappearance of a spot of linoleyl alcohol was ascertained through TLC (chloroform development, phosphoric acid-copper sulfate color development). Ethanol (5.2 g, 113 mmol) was added, and triethylamine hydrochloric acid salts were filtrated. The filtrate was washed with ion-exchanged water (150 g), and the water layer was discarded. The same operation of washing with ion-exchanged water was performed again. The organic layer was dehydrated with anhydrous magnesium sulfate (20 g) and, thereafter, filtration and concentration were performed, so as to obtain linoleyl methane sulfonate (amount of production: 120 g, yield: 93%).

Workup

  1. custombecame 30° C.
  2. customOne hour
  3. aliquotthe reaction solution was sampled
  4. filtrationtriethylamine hydrochloric acid salts were filtrated
  5. washThe filtrate was washed with ion-exchanged water (150 g)
  6. washThe same operation of washing with ion-exchanged water
  7. filtrationfiltration and concentration

Sources & evidence

ORD record
ord-55f014e1212e4465944d5ffedb16d44f
Source dataset
uspto-grants-2016_06
Patent number
US09371271B2

Reaction notes

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