Dimethyl Sulfoxide → Dilauryl disulfide

HRID 1075996Notes

Reaction equation

HRID 1075996 reaction equation
C[S:2]([CH3:4])=O.[CH2:5]([SH:17])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]>Cl.II>[CH2:5]([S:17][S:2][CH2:4][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH3:5])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 2

HCID 679Dimethyl SulfoxideHCID 81951-Dodecanethiol

Product 1

HCID 151040Dilauryl disulfideYield 90%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 807IodineCatalyst

Conditions

Temperature
60 °C

Procedure

A mixture of 9 ml of DMSO (127 mmole), 12 ml of 1-dodecanethiol (50 mmole), 0.1 ml of 37 percent hydrochloric acid (1.2 mmole), and 10.8 mg of iodine (0.085 mmole as HI) was heated by a bath, while stirring magnetically, at about 60°C. After one and a fourth hours, the lower phase became amber colored. The mixture was cooled with stirring to produce fine crystals. These were filtered off and rinsed with DMSO. Recrystallization from acetone gave 9.02 g of didodecyl disulfide (90 percent of theory). Mp, 33°-5°C. (reported, 33°-4°C.).

Workup

  1. temperaturewas heated by a bath
  2. temperatureThe mixture was cooled
  3. stirringwith stirring
  4. customto produce fine crystals
  5. filtrationThese were filtered off
  6. washrinsed with DMSO
  7. customRecrystallization from acetone

Sources & evidence

ORD record
ord-600f13a40cc94b9597245da9428a9f42
Source dataset
uspto-grants-1976_05
Patent number
US03954800

Reaction notes

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