Epichlorohydrin → Tert-octylglycidyl thioether

HRID 443046Notes

Reaction equation

HRID 443046 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 at 15° to 20° C. in the course of 70 minutes, with stirring and partial cooling (especially 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 further stirred for 1 hour at 50° C.; 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 in the form of 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. additionespecially at the commencement of the addition),
  3. stirringThe reaction mixture is further stirred for 1 hour at 50° C.
  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-8173d694907c48ed97bf5ac890961f27
Source dataset
uspto-grants-1999_04
Patent number
US05892051

Reaction notes

Loading…