2-(Chloroethoxy)ethanol → 2,2'-{Sulfanediylbis[(ethane-2,1-diyl)oxy]}di(ethan-1-ol)

HRID 580308Notes

Reaction equation

HRID 580308 reaction equation
[S-2:1].[Na+].[Na+].Cl[CH2:5][CH2:6][O:7][CH2:8][CH2:9][OH:10]>>[OH:10][CH2:9][CH2:8][O:7][CH2:6][CH2:5][S:1][CH2:5][CH2:6][O:7][CH2:8][CH2:9][OH:10]

Participants

3

Reactant 2

HCID 123612-(Chloroethoxy)ethanolHCID 14804Sodium Sulfide

Product 1

HCID 3355552,2'-{Sulfanediylbis[(ethane-2,1-diyl)oxy]}di(ethan-1-ol)

Procedure

The reaction between sodium sulfide and two moles of 2-(2'-chloroethoxy)ethanol yields the intermediate compound 1,11-dihydroxy-3,9-dioxa-6-thiaundecane; ##STR5## Halogenation of the thiaundecane intermediate with thionyl chloride in dimethylsulfoxide (DMF) yields Intermediate A: ##STR6## Condensation of Intermediate A with 1,5-dimercapto-3-oxapentane in an aqueous-ethanol solution of sodium carbonate yields Compound 3: ##STR7##

Sources & evidence

ORD record
ord-110cf62db8214c5d9a0201ed228f734d
Source dataset
uspto-grants-1988_06
Patent number
US04752560

Reaction notes

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