Ethyl Acetate → Ethanol ethylacetate

HRID 496290Notes

Reaction equation

HRID 496290 reaction equation
C(O)(=O)/C=[CH:3]\[C:4](O)=[O:5].[C:9]([O:12][CH2:13][CH3:14])(=[O:11])[CH3:10]>C(O)C>[CH2:4]([OH:5])[CH3:3].[C:9]([O:12][CH2:13][CH3:14])(=[O:11])[CH3:10]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 444266Maleic Acid

Product 1

HCID 21584252Ethanol ethylacetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The amine compound of Formula I (10 g) in ethyl acetate (35 mL) was mixed with a solution of maleic acid (2.18 g) in ethanol (10 mL) at room temperature. Crystalline seeds were added and the mixture was stirred at room temperature for 22 h. The slurry was cooled gradually to −10° C. and stirred at that temperature for 4 h. The product was filtered, washed with ethyl acetate (10 mL), and dried overnight at 64° C. under vacuum to give the desired salt as a white solid. Ratio of rotamer 1 to 2: 2.3:97.7.

Workup

  1. additionCrystalline seeds were added
  2. temperatureThe slurry was cooled gradually to −10° C.
  3. stirringstirred at that temperature for 4 h
  4. filtrationThe product was filtered
  5. washwashed with ethyl acetate (10 mL)
  6. customdried overnight at 64° C. under vacuum

Sources & evidence

ORD record
ord-ee26a4eb7fe54867a18dbfeaf3632b0f
Source dataset
uspto-grants-2005_09
Patent number
US06943251B2

Reaction notes

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