Ethyl Acetate → Isopropanol ethyl acetate

HRID 496291Notes

Reaction equation

HRID 496291 reaction equation
C(O)(=O)/C=[CH:3]\[C:4]([OH:6])=O.[C:9]([O:12][CH2:13][CH3:14])(=[O:11])[CH3:10]>C(O)(C)C>[CH:4]([OH:6])([CH3:3])[CH3:9].[C:9]([O:12][CH2:13][CH3:14])(=[O:11])[CH3:10]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 444266Maleic Acid

Product 1

HCID 22055037Isopropanol ethyl acetate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
40 °C

Procedure

The amine compound of Formula I (10 g) in ethyl acetate (40 mL) was mixed with a solution of maleic acid (2.2 g) in isopropanol (20 mL) at 55° C. The cloudy mixture was seeded, cooled slowly to 40° C., and stirred at 40° C. overnight. The resulting slurry was cooled gradually to room temperature and stirred overnight. The product was filtered, washed with 2:1 ethyl acetate/isopropanol (30 mL), and dried overnight at 55° C. under vacuum to give the desired salt as a white solid. Ratio of rotamers 1 to 2: 0.9:99.1.

Workup

  1. temperatureThe resulting slurry was cooled gradually to room temperature
  2. stirringstirred overnight
  3. filtrationThe product was filtered
  4. washwashed with 2:1 ethyl acetate/isopropanol (30 mL)
  5. customdried overnight at 55° C. under vacuum

Sources & evidence

ORD record
ord-2257d062e21346e7a2995bd1956f5a2a
Source dataset
uspto-grants-2005_09
Patent number
US06943251B2

Reaction notes

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