1-(2-butoxyethoxy)ethanol

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

Procedure: 248.2 g. (0.8 mol) of triphenyl phosphite and 131.2 g (0.81 mol) of 2-butoxyethoxyethanol were put into a flask of 500 ml. and 0.1 g. of sodium hydroxide was added thereto to react at 140°C. for 4 hours. The liberated phenol was distilled away by distillation under a reduced pressure (at 60°C. under 5 mm.Hg). Then the residual solution was filtered to obtain colorless transparent 2-(2-butoxyethoxy)ethyl diphenyl phosphite (Compound 9) as a filtrate. to react at 140°C. for 4 hours The liberated phenol was distilled away by distillation under a reduced pressure (at 60°C. under 5 mm.Hg) Then the residual solution was filtered

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

Procedure: A mixture of 400 g triethylene glycol monoethyl ether (2.2 mol), 48 g paraformaldehyde (1.6 mol), 150 ml toluene and 10 g of an acid ion exchange resin was refluxed for 6 hours in a 1 liter flask equipped with a water separator and reflux condenser. Filtration of the product followed by distillation gave a quantitative yield of the desired product. was refluxed for 6 hours in a 1 liter flask reflux condenser Filtration of the product followed by distillation

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

Procedure: A mixture of 400 g triethylene glycol monoethyl ether (2.2 mol), 48 g paraformaldehyde (1.6 mol), 150 ml toluene and 10 g of an acid ion exchange resin was refluxed for 6 hours in a 1 liter flask equipped with a water separator and reflux condenser. Filtration of the product followed by distillation gave a quantitative yield of the desired product. was refluxed for 6 hours in a 1 liter flask reflux condenser Filtration of the product followed by distillation

Conditions: temp:6.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Thioglycolic acid (40.9 ml, 0.589 mole) obtained from Evans Chemetics, Inc. was added dropwise with stirring to butoxyethoxyethanol (butyl Carbitol) (95.53 g, 0.589 mole) obtained from Fisher Scientific Company with 12% Dowex cation exchange resin HGR-W (10% crosslinking, 11.46 g) as a catalyst. A temperature increase of 6° C. occurred immediately upon addition of the reactants. The solution was further heated and the byproduct, water, was distilled over at 89° C. and collected. When 50% of the water had been collected, a 30% excess of butoxyethoxyethanol (33 mls) was added to increase the rate of product formation. After 3.5 hours a 92.4% yield of butoxyethoxyethyl thioglycolate was obtained and thereafter vacuum distilled at 10 mm Hg and a temperature range of 25°-100° C. in order to remove the unreacted starting materials. was added dropwise occurred immediately upon addition of the reactants The solution was further heated the byproduct, water, was distilled over at 89° C. collected When 50% of the water had been collected a 30% excess of butoxyethoxyethanol (33 mls) was added to increase the rate of product formation