Triethylamine → Oleyl methane sulfonate

HRID 1499370Notes

Reaction equation

HRID 1499370 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][CH2:12][CH2:13][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(Cl)Cl>[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][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])(=[O:30])=[O:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 5284499Oleyl Alcohol2×

Product 1

HCID 6016198Oleyl methane sulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Oleyl alcohol, also called cis 9 octadecen-1-ol, (100 g, 0.37M) was dissolved in DCM, dichloromethane and cooled to 0° C. Triethylamine (56.5 g, 78 ml, 0.56M, 1.5 equivalents) was added to the solution at this temperature and the mixture was stirred for one hour. Methanesulphonyl chloride (47 g, 31.8 ml, 1.1 equivalents) was then added to the mixture at this temperature and the mixture was stirred at 0° C. for 30 minutes before being allowed to warm to room temperature. The reaction mixture was washed with ice/water, cold 10% hydrochloric acid, cold solution of sodium bicarbonate, water and brine successively, then dried with sodium sulphate. After filtration, the solvent was removed under vacuum to yield and oil which was chilled overnight to yield a solid with a low melting point (yield 126.5 g, 99%).

Workup

  1. stirringthe mixture was stirred at 0° C. for 30 minutes
  2. washThe reaction mixture was washed with ice/water, cold 10% hydrochloric acid, cold solution of sodium bicarbonate, water and brine successively
  3. dry with materialdried with sodium sulphate
  4. filtrationAfter filtration
  5. customthe solvent was removed under vacuum
  6. customto yield
  7. temperatureoil which was chilled overnight
  8. customto yield a solid with a low melting point (yield 126.5 g, 99%)

Sources & evidence

ORD record
ord-306aed2d1d094e0cab53514eda5991a8
Source dataset
uspto-grants-2015_12
Patent number
US09200229B2

Reaction notes

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