Methyl acetoacetate → HCID 22483921, compound

HRID 1838632Notes

Reaction equation

HRID 1838632 reaction equation
[Na].[C:2]([O:8]C)(=O)[CH2:3][C:4]([CH3:6])=[O:5].[F:10][C:11]([F:22])([F:21])[C:12]([CH3:20])=[CH:13]C(OC(C)C)=O>C(O)C>[CH3:13][C:12]1([C:11]([F:22])([F:21])[F:10])[CH2:20][C:2](=[O:8])[CH2:3][C:4](=[O:5])[CH2:6]1

Participants

5

Reactant 3

HCID 7757Methyl acetoacetateHCID 5360545SodiumHCID 86592581HCID 86592581, compound

Product 1

HCID 22483921HCID 22483921, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.64 g of sodium were introduced into 40 ml of ethanol, and 3.23 ml of methyl acetoacetate and 4.9 g of isopropyl 4,4,4-trifluoro-3-methylbut-2-enoate were introduced, and the mixture was heated at the boil for 18 hours. After the mixture has been partitioned between dilute hydrochloric acid and ethyl acetate, the mixture is evaporated. The remaining unpurified methyl 2-methyl-4,6-dioxo-2-trifluoromethylcyclohexanecarboxylate is hydrolysed in a mixture of methanol and water at boiling point in the presence of 9.1 g of sodium hydroxide. The mixture is subsequently acidified with hydrochloric acid and extracted with fresh ethyl acetate. After recrystallization (ethyl acetate), pure 5-methyl-5-trifluoromethylcyclohexane-1,3-dione of melting point 150-152° C. is obtained.

Workup

  1. additionwere introduced
  2. temperaturethe mixture was heated at the boil for 18 hours
  3. customAfter the mixture has been partitioned between dilute hydrochloric acid and ethyl acetate
  4. customthe mixture is evaporated
  5. additionThe remaining unpurified methyl 2-methyl-4,6-dioxo-2-trifluoromethylcyclohexanecarboxylate is hydrolysed in a mixture of methanol and water
  6. extractionextracted with fresh ethyl acetate
  7. customAfter recrystallization (ethyl acetate), pure 5-methyl-5-trifluoromethylcyclohexane-1,3-dione of melting point 150-152° C.
  8. customis obtained

Sources & evidence

ORD record
ord-e2516a34e9b64c44b5bdea785b2457ce
Source dataset
uspto-grants-2004_01
Patent number
US06673938B1

Reaction notes

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