p-Toluenesulfonic acid → 2,3,5,6,7,8-Hexahydro-1,4-benzodithiine

HRID 2058804Notes

Reaction equation

HRID 2058804 reaction equation
OC1CCCCC1=O.[CH:9](S)([SH:11])[CH3:10].[C:13]1(C)[CH:18]=[CH:17][C:16]([S:19](O)(=O)=O)=[CH:15][CH:14]=1>>[S:19]1[C:16]2[CH2:17][CH2:18][CH2:13][CH2:14][C:15]=2[S:11][CH2:9][CH2:10]1

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 10785Cyclohexanone, 2-hydroxy-HCID 336451,1-Ethanedithiol

Product 1

HCID 3229032,3,5,6,7,8-Hexahydro-1,4-benzodithiineYield 75.1%

Procedure

The method of Example 4 was used, using 2-hydroxycyclohexanone (10 g), ethane dithiol (8.3 g) and p-toluenesulphonic acid to give 5,6,7,8-tetrahydro-1,4-benzodithian as a brownish oil (not distilled), yield 75.1%. NMR (CDCl3) 3.14 δ, 1.5-2.3 δ (two overlapping complex multiplets).

Sources & evidence

ORD record
ord-f5bc392fd0ce4aeaa5585f0d5ee0f1da
Source dataset
uspto-grants-1982_03
Patent number
US04319033

Reaction notes

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