Trifluoromethanesulfonic acid, lithium salt → 5-Cyclohexadecen-1-one

HRID 905135Notes

Reaction equation

HRID 905135 reaction equation
[CH:1]([C:3]1([OH:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[CH:15]=[CH2:16])=[CH2:2].FC(F)(F)S([O-])(=O)=O.[Li+]>C(Cl)Cl>[C:3]1(=[O:17])[CH2:1][CH2:2][CH2:16][CH2:15][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH:11][CH2:12][CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 3664839Trifluoromethanesulfonic acid, lithium saltHCID 11096619Cyclododecanol, 1,2-diethenyl-

Product 1

HCID 1622685-Cyclohexadecen-1-oneYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1,2-divinylcyclododecan-1-ol (0.125 g, 5.10-4 mol), lithium trifluoromethanesulphonate (0.080 g) and mercuric trifluoroacetate (0.045 g) in methylene chloride (5 cc) is kept at a temperature of the order of 20° C. for 20 minutes. The reaction mixture is washed with a saturated aqueous solution of sodium bicarbonate (3×10 cc) and then extracted with methylene chloride (3×10 cc). The organic extracts are dried over magnesium sulphate. After filtration and concentration to dryness under reduced pressure (20 mm Hg; 2.7 kPa), cyclohexadec-5-en-1-one (0.085 g) is obtained with a yield of 69%.

Workup

  1. washThe reaction mixture is washed with a saturated aqueous solution of sodium bicarbonate (3×10 cc)
  2. extractionextracted with methylene chloride (3×10 cc)
  3. dry with materialThe organic extracts are dried over magnesium sulphate
  4. filtrationAfter filtration and concentration to dryness under reduced pressure (20 mm Hg; 2.7 kPa)

Sources & evidence

ORD record
ord-348fb71411c0438590881079a8c91bf8
Source dataset
uspto-grants-1983_12
Patent number
US04421934

Reaction notes

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