Epichlorohydrin → Tert-octylglycidyl thioether

HRID 2106905Notes

Reaction equation

HRID 2106905 reaction equation
[OH-].[Na+].[C:3]([SH:11])([CH2:6][C:7]([CH3:10])([CH3:9])[CH3:8])([CH3:5])[CH3:4].[CH2:12]([CH:14]1[O:16][CH2:15]1)Cl>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:3]([S:11][CH2:12][CH:14]1[O:16][CH2:15]1)([CH2:6][C:7]([CH3:10])([CH3:9])[CH3:8])([CH3:5])[CH3:4]

Participants

6

Reactant 3

HCID 7835EpichlorohydrinHCID 8851tert-OCTYL MERCAPTANHCID 14798Sodium Hydroxide

Product 1

HCID 85528098Tert-octylglycidyl thioether

Reagents, catalysts & solvents 2

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 962WaterSolvent

Procedure

A solution of 66 parts by weight of sodium hydroxide, 300 parts by weight of water and 8 parts by weight of tetrabutylammonium chloride is added dropwise within 70 minutes at 15° to 20° C., with stirring and partial cooling (particularly at the commencement of the addition) to a mixture of 219 parts by weight of tert-octylmercaptan and 135 parts by weight of epichlorohydrin. The reaction mixture is subsequently stirred at 50° C. for 1 hour; the aqueous phase is then separated, and the organic phase is washed with 200 parts by weight of water. The organic phase is finally distilled in vacuo to thus obtain the tert-octylglycidyl thioether as a colourless liquid having a boiling point of 74° to 75° C. at 0.02 mbar, and a refractive index of nD20 =1.4803; the yield is 250 parts by weight, which corresponds to 82% of the theoretical yield.

Workup

  1. temperaturepartial cooling (
  2. additionparticularly at the commencement of the addition)
  3. stirringThe reaction mixture is subsequently stirred at 50° C. for 1 hour
  4. customthe aqueous phase is then separated
  5. washthe organic phase is washed with 200 parts by weight of water
  6. distillationThe organic phase is finally distilled in vacuo

Sources & evidence

ORD record
ord-48b18d3f90654a9a852c2937e3ac950f
Source dataset
uspto-grants-1990_06
Patent number
US04931576

Reaction notes

Loading…