1,3-Propanedithiol → 2-[4-(4,4,4-trifluorobutoxy)phenyl]-5,6-dihydro-4H-1,3-dithiin-1-ium trifluoromethanesulfonate

HRID 511700Notes

Reaction equation

HRID 511700 reaction equation
[F:1][C:2]([F:17])([F:16])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11](O)=O)=[CH:9][CH:8]=1.[CH2:18]([SH:22])[CH2:19][CH2:20][SH:21].[F:23][C:24]([F:30])([F:29])[S:25]([OH:28])(=[O:27])=[O:26]>C(CC(C)(C)C)(C)C.C1(C)C=CC=CC=1>[F:23][C:24]([F:30])([F:29])[S:25]([O-:28])(=[O:27])=[O:26].[F:1][C:2]([F:17])([F:16])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]2[S:22][CH2:18][CH2:19][CH2:20][S+:21]=2)=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 80131,3-PropanedithiolHCID 62406Trifluoromethanesulfonic acidHCID 223614014-(4,4,4-Trifluorobutoxy)benzoic acid

Product 1

HCID 866765372-[4-(4,4,4-trifluorobutoxy)phenyl]-5,6-dihydro-4H-1,3-dithiin-1-ium trifluoromethanesulfonateYield 94.9%

Reagents, catalysts & solvents 1

HCID 21883168Isooctane tolueneSolvent

Procedure

60 g (242 mmol) of 4-(4,4,4-trifluorobutoxy)benzoic acid, 31.8 ml (314 mmol) of propane-1,3-dithiol and 27.9 ml (314 mmol) of trifluoromethanesulfonic acid are refluxed in 1.61 of a mixture 1/1 isooctane/toluene for 18 hours. The mixture is cooled down and the product is precipitated by addition of 1.5 l of TBME to yield 108 g of 2-[4-(4,4,4-trifluorobutoxy)phenyl]-5,6-dihydro-4H-1,3-dithiin-1-ium trifluoromethanesulfonate as yellow crystals.

Workup

  1. temperatureThe mixture is cooled down
  2. customthe product is precipitated by addition of 1.5 l of TBME

Sources & evidence

ORD record
ord-90052f0712904c61956c6fb3f9fdd6f6
Source dataset
uspto-grants-2015_08
Patent number
US09097938B2

Reaction notes

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