p-Toluenesulfonic acid → HCID 131723764, compound

HRID 1059046Notes

Reaction equation

HRID 1059046 reaction equation
C(C1SCCS1)CCCC.[S].C1(C)C=CC(S(O)(=O)=O)=CC=1.[H][H].CCCCCCSCCS.[CH3:35][O:36][Si:37]([O:47][CH3:48])([O:45][CH3:46])[CH2:38][CH2:39][CH:40]1[S:44][CH2:43][CH2:42][S:41]1>C1(C)C=CC=CC=1>[Si:37]([CH2:38][CH2:39][CH2:40][S:41][CH2:42][CH2:43][SH:44])([O:47][CH3:48])([O:36][CH3:35])[O:45][CH3:46]

Participants

8

Reactant 6

HCID 6101p-Toluenesulfonic acidHCID 5362487SulfurHCID 98341081,3-Dithiolane, 2-pentyl-HCID 12070523HCID 12070523, compoundHCID 57035733HCID 57035733, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131723764HCID 131723764, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Into a 300 ml rocking autoclave were charged 58.2 g (0.331 m) of 2-(n-pentyl)-1,3-dithiolane, 1.06 g of sulfur, 0.12 g of p-toluenesulfonic acid, and 1.87 g of cobalt polysulfide catalyst (added as a 43% slurry in toluene). The autoclave was pressurized with hydrogen and maintained between 1600 and 2200 psi while being heated to 250°. After cooling and venting, the crude product contained 57% of the hydrogenolysis product, CH3(CH2)5S(CH2)2SH, as determined by GC/MS. When this procedure is applied to the product of Example 1, the hydrogenolysis product, (MeO)3Si(CH2)3S(CH2)2SH, is obtained.

Workup

  1. temperaturemaintained between 1600 and 2200 psi
  2. temperaturewhile being heated to 250°
  3. temperatureAfter cooling

Sources & evidence

ORD record
ord-0bb27f2e35774abea7c25de39fa783bf
Source dataset
uspto-grants-2003_02
Patent number
US06518335B2

Reaction notes

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