Sodium Iodide → 1-Methylthioheptadecan-2-one

HRID 2412620Notes

Reaction equation

HRID 2412620 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[CH3:14][S:15]([CH2:17][C:18](=[O:34])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=O.[I-].[Na+]>CC(C)=O>[CH3:14][S:15][CH2:17][C:18](=[O:34])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 9845Trifluoroacetic anhydrideHCID 124884111-Methylsulphinylheptadecan-2-one

Product 1

HCID 124884131-Methylthioheptadecan-2-oneYield 86.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of trifluoroacetic anhydride (1.68 g) in acetone (5 ml) was added to a stirred mixture of 1-methylsulphinylheptadecan-2-one (1.58 g) and sodium iodide (1.8 g) in acetone (10 ml) cooled in an ice bath. The mixture was stirred for a further 10 minutes and then evaporated. Water (50 ml) was added to the residue and the mixture was extracted with diethyl ether (2×40 ml). The ether extract was washed with a solution of sodium thiosulphate (3 g) in water (50 ml), dried over magnesium sulphate and evaporated to give 1-methylthioheptadecan-2-one (1.3 g), m.p. 40° C.

Workup

  1. temperaturecooled in an ice bath
  2. customevaporated
  3. additionWater (50 ml) was added to the residue
  4. extractionthe mixture was extracted with diethyl ether (2×40 ml)
  5. extractionThe ether extract
  6. washwas washed with a solution of sodium thiosulphate (3 g) in water (50 ml)
  7. dry with materialdried over magnesium sulphate
  8. customevaporated

Sources & evidence

ORD record
ord-089015b60b0d469597c4a87542bdbebf
Source dataset
uspto-grants-1985_01
Patent number
US04493843

Reaction notes

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