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

HRID 325997Notes

Reaction equation

HRID 325997 reaction equation
[C:1]([OH:5])(=[O:4])[CH:2]=[O:3].[CH2:6]([OH:10])[CH2:7][CH2:8][CH3:9]>>[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

3

Reactant 2

HCID 2631-Butanol2×HCID 760Glyoxylic Acid

Product 1

HCID 109478Acetic acid, 2-butoxy-2-hydroxy-, butyl esterYield 2%

Procedure

Aqueous glyoxylic acid (50%) in the amount of 1,980 parts (13.3 moles) and butanol in the amount of 1,210 parts (16.4 moles) are heated at 55°-60° C. and stripped under vacuum. Butanol in the amount of 1,210 parts (16.4 moles) is added and the reaction is heated at 80°-85° C. under reflux at reduced pressure for two hours. Volatiles are removed at 55°-60° C. under vacuum. Butanol in the amount of 807 parts (10.9 moles) is added and the reaction mixture is refluxed at 80°-85° C. under reduced pressure for six hours. Volatiles are again removed at 55°-60° C. under vacuum to yield 2,850 parts of butyl glyoxylate butyl hemiacetal containing about 2% butyl glyoxylate dibutyl acetal. To the crude hemiacetal (765 parts 3.0 moles) are added monomethyl ether of hydroquinone (0.65 parts and acrylamide (213 parts 3.0 moles). The reaction mixture is heated at 70°-75° C. for three hours. Three intermediate strippings under vacuum removes byproduct butanol (164 parts 2.2 moles). Methanol (870 parts, 25.5 moles) containing sulfuric acid (5.5 parts, 0.056 mole) is added. The reaction mixture is refluxed for 30 minutes and then wet methanol and butane were allowed to distill while fresh methanol (475 parts, 14.0 moles) is added in proportions approximately equal to the amount removed. The reaction mixture is then heated under reflux for an additional two hours. Treatment as described in Example 1 and neutralization of sulfuric acid catalyst with lithium oxide yielded 741 parts of orange colored liquid. Analysis of proton magnetic resonance shows the product contains approximately 90-95% methyl ether and methyl ester groups.

Workup

  1. temperaturethe reaction is heated at 80°-85° C.
  2. temperatureunder reflux at reduced pressure for two hours
  3. customVolatiles are removed at 55°-60° C. under vacuum
  4. additionButanol in the amount of 807 parts (10.9 moles) is added
  5. temperaturethe reaction mixture is refluxed at 80°-85° C. under reduced pressure for six hours
  6. customVolatiles are again removed at 55°-60° C. under vacuum

Sources & evidence

ORD record
ord-f973273fb9e64252a0602408b2762a05
Source dataset
uspto-grants-1984_04
Patent number
US04443623

Reaction notes

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