Hexane → HCID 86735621, compound

HRID 2083186Notes

Reaction equation

HRID 2083186 reaction equation
[CH2:1]([O:5][C:6]([S:8]Cl)=[O:7])[CH2:2][CH2:3][CH3:4].[CH3:10][O:11][C:12]([S:14]Cl)=[O:13].ClC(SCl)=O.[CH2:21]([SH:30])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][SH:29].[CH3:31][CH2:32][CH2:33]CCC>C(O)CCC>[CH2:1]([O:5][C:6]([S:8][S:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][S:30][S:14][C:12]([O:11][CH2:10][CH2:31][CH2:32][CH3:33])=[O:13])=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 5

HCID 8058Hexane2×HCID 144931,8-OctanedithiolHCID 75990(Chlorothio)formyl chlorideHCID 123417Thiocarbonic acid, anhydrosulphide with methyl thiohypochloriteHCID 12418459HCID 12418459, compound2×

Product 1

HCID 86735621HCID 86735621, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
0 °C

Procedure

1-Butoxycarbonylsulfenyl chloride, with a boiling point of 83°-90° C. at 13 mm., was prepared in 84.3% yield by a procedure analogous to that described for methoxycarbonylsulfenyl chloride in Example I by reacting equimolar quantities of 1-butanol and chlorocarbonylsulfenyl chloride. To a stirred solution of 8.4 grams (0.05 mole) of 1-butoxycarbonylsulfenyl chloride and 25 milliliters of hexane was added dropwise with stirring and under nitrogen at 0° C., 4.4 grams (0.025 mole) of 1,8-octanedithiol dissolved in 25 milliliters of hexane. After allowing the solution to warm to room temperature, the solution was concentrated under reduced pressure to give 10.9 grams (98.2%) of 1,8-bis(1-butoxycarbonyldithio)-octane as a pale yellow liquid.

Workup

  1. custom, was prepared in 84.3% yield by a procedure analogous to
  2. temperatureto warm to room temperature
  3. concentrationthe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-772e5b3eb3664a67beadea93e1e62a2f
Source dataset
uspto-grants-1978_04
Patent number
US04085094

Reaction notes

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