1-Butanol → Acetic acid, 2-butoxy-2-hydroxy-, butyl ester

HRID 1602559Notes

Reaction equation

HRID 1602559 reaction equation
[C:1]([OH:5])(=[O:4])[CH:2]=[O:3].[CH2:6]([OH:10])[CH2:7][CH2:8][CH3:9]>O>[CH2:6]([O:4][CH:1]([OH:5])[C:2]([O:10][CH2:6][CH2:7][CH2:8][CH3:9])=[O:3])[CH2:7][CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 2631-ButanolHCID 760Glyoxylic Acid

Product 1

HCID 109478Acetic acid, 2-butoxy-2-hydroxy-, butyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
82.5 °C

Procedure

In a suitable reactor flask equipped with stirrer, heating mantle, Dean Stark trap, condenser, nitrogen inlet, vacuum take off and dropping funnel were added 1980 grams (13.0 moles) of 50% glyoxylic acid in water and 1215 grams (16.4 moles) of n-butanol. The contents of the flask were heated to 80-85° C. under nitrogen sparge and vacuum to remove approximately 760 grams of an n-butanol/water azeotrope. Thereafter, an additional 1210 grams of n-butanol were added and strip distillation continued until no water was seen in the azeotrope. An additioral 810 grams of n-butanol were then added and the mixture refluxed for two hours at 80-85° C. under vacuum, followed by vacuum stripping of excess n-butanol. Product weight was 2850 grams.

Workup

  1. customIn a suitable reactor flask equipped with stirrer
  2. temperatureheating mantle, Dean Stark trap, condenser, nitrogen inlet, vacuum
  3. customsparge
  4. customvacuum to remove approximately 760 grams of an n-butanol/water
  5. additionThereafter, an additional 1210 grams of n-butanol were added
  6. distillationstrip distillation
  7. additionAn additioral 810 grams of n-butanol were then added
  8. temperaturethe mixture refluxed for two hours at 80-85° C. under vacuum

Sources & evidence

ORD record
ord-a5fcd244962243f6ad1e1a53da0a5972
Source dataset
uspto-grants-1999_11
Patent number
US05981648

Reaction notes

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