1-(2-chloroethoxy)-2-[2-(2-chloroethoxy)ethoxy]ethane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: This compound is obtained by reacting 1,11-dichloro-3,6,9-trioxaundecane with 1,5-dimercapto-3-thiapentane in the presence of sodium carbonate in aqueous ethanol: ##STR8## This compound is obtained

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: This compound is obtained by reacting 1,11-dichloro-3,6,9-trioxaundecane with 1,5-dimercapto-3-thiapentane in the presence of sodium carbonate in aqueous ethanol: ##STR8## This compound is obtained

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 10 g (0.037 mole) bis(2-hydroxy-5-chlorophenyl)-methane and 8.6 g (0.037 mole) 1,11-dichloro-3,6,9-trioxaundecane are dissolved in 100 ml n-BuOH. To this is added 6.5 g 50% aqueous sodium hydroxide. The resulting solution is heated to reflux for 15 hours, acidified with ethereal HCl, and solvent stripped in vacuo. The resulting gum is chromatographed on Neutral Alumina IV, eluting with ether/ethyl acetate. Appropriate fractions are collected, combined and recrystallized from methanol to yield 3.65 g white crystalline solid; m.p. 143.5°-144°. Yield: 23%. The resulting solution is heated to reflux for 15 hours The resulting gum is chromatographed on Neutral Alumina IV eluting with ether/ethyl acetate Appropriate fractions are collected recrystallized from methanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 430 g of tetraethylene glycol (2.2 moles), 2000 ml of dry benzene, and 386 g of pyridine (4.9 moles) is heated to reflux, and 580 g of thionyl chloride (4.9 moles) is added dropwise with stirring in three hours. During this period the reflux temperature of the mixture drops from 86° to 78°, and a white precipitate is formed. Heating is continued overnight (16 hours) and, after cooling, 50 ml of hydrochloric acid diluted with 200 ml of water is added dropwise in about 15 minutes. Benzene is removed from the upper layer containing the product, and the residue vacuum distilled at 4.5 mm Hg at 165°. The yield is 375 g of light yellow liquid (72%). is heated to reflux During this period the reflux temperature of the mixture drops from 86° to 78° a white precipitate is formed Heating is continued overnight (16 hours) and, after cooling is added dropwise in about 15 minutes Benzene is removed from the upper layer containing the product the residue vacuum distilled at 4.5 mm Hg at 165°

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: This compound is obtained by reacting 1,11-dichloro-3,6,9-trioxaundecane with 1,5-dimercapto-3-thiapentane in the presence of sodium carbonate in aqueous ethanol: ##STR8## This compound is obtained