Thioglycolic Acid → Butoxyethoxyethyl thioglycolate

HRID 1277854Notes

Reaction equation

HRID 1277854 reaction equation
[C:1]([OH:5])(=[O:4])[CH2:2][SH:3].[CH2:6]([O:10][CH2:11][CH2:12][O:13][CH:14](O)[CH3:15])[CH2:7][CH2:8][CH3:9]>>[C:1]([O:5][CH2:15][CH2:14][O:13][CH2:12][CH2:11][O:10][CH2:6][CH2:7][CH2:8][CH3:9])(=[O:4])[CH2:2][SH:3]

Participants

3

Reactant 2

HCID 1133Thioglycolic AcidHCID 410881-(2-Butoxyethoxy)ethanol

Product 1

HCID 54112028Butoxyethoxyethyl thioglycolateYield 92.4%

Conditions

Temperature
6 °C

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.

Workup

  1. additionwas added dropwise
  2. additionoccurred immediately upon addition of the reactants
  3. temperatureThe solution was further heated
  4. distillationthe byproduct, water, was distilled over at 89° C.
  5. customcollected
  6. customWhen 50% of the water had been collected
  7. additiona 30% excess of butoxyethoxyethanol (33 mls) was added
  8. temperatureto increase the rate of product formation

Sources & evidence

ORD record
ord-010e72a665d04c2b983b415dea196a5d
Source dataset
uspto-grants-1981_07
Patent number
US04279806

Reaction notes

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