Hydrogen Sulfide → HCID 131712563, compound
Reaction equation
O.[SH2:2].[Na].S.[CH2:5]([O:9][CH2:10][CH:11]([CH2:16][CH3:17])[CH2:12][CH2:13][CH2:14][CH3:15])[CH:6]1[O:8]C1.[CH3:18]O>>[CH2:16]([CH:11]([CH2:12][CH2:13][CH2:14][CH3:15])[CH2:10][O:9][CH:5]([CH2:6][OH:8])[CH2:18][SH:2])[CH3:17]Participants
Procedure
5 g of solid sodium hydrogen sulfide monohydrate are saturated with hydrogen sulfide at room temperature in 250 ml of methanol. Then 186 g (1 mole) of 2-ethylhexyl glycidyl ether are added dropwise at room temperature and with efficient stirring in the course of 2 hours, while simultaneously introducing hydrogen sulfide gas. The flow of hydrogen sulfide gas is constantly introduced in an amount just sufficient for the reaction solution to take up. The temperature should not exceed 30°-40° C. in order effectively to prevent the formation of corresponding thioethers. When the reaction of the epoxide is complete, the catalyst is destroyed with a small amount of dilute sulfuric acid and the reaction mixture is extracted with ether. The ethereal extract is washed neutral with water, dried over magnesium sulfate and the solvent is removed. Distillation of the residue at 75° C./10-3 torr yields the pure monothioglycerol 2-ethylhexyl ether with a SH content of 14.8%.
Workup
- customexceed 30°-40° C. in order
- customthe catalyst is destroyed with a small amount of dilute sulfuric acid
- extractionthe reaction mixture is extracted with ether
- extractionThe ethereal extract
- washis washed neutral with water
- dry with materialdried over magnesium sulfate
- customthe solvent is removed
- distillationDistillation of the residue at 75° C./10-3 torr
Sources & evidence
- ORD record
- ord-f57eef143529489987d34809c21a316f
- Source dataset
- uspto-grants-1982_01
- Patent number
- US04310454
Reaction notes
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