Ethanol → HCID 22483921, compound

HRID 2180905Notes

Reaction equation

HRID 2180905 reaction equation
[Na].CO[C:4](=[O:6])[CH3:5].C(O[C:11](=[O:19])[CH:12]=[C:13]([CH3:18])[C:14]([F:17])([F:16])[F:15])(C)C.[CH2:20](O)C>>[CH3:18][C:13]1([C:14]([F:15])([F:16])[F:17])[CH2:5][C:4](=[O:6])[CH2:20][C:11](=[O:19])[CH2:12]1

Participants

5

Reactant 4

HCID 702EthanolHCID 6584Methyl AcetateHCID 5360545SodiumHCID 86592581HCID 86592581, compound

Product 1

HCID 22483921HCID 22483921, compound

Procedure

0.64 g of sodium is introduced into 40 ml of ethanol, 3.23 ml of acetic acid methyl ester and 4.9 g of 4,4,4-trifluoro-3-methyl-but-2-enoic acid isopropyl ester are incorporated and the mixture is heated at boiling temperature for 18 hours. After extraction with dilute hydrochloric acid against ethyl acetate, concentration by evaporation is carried out. The non-purified 2-methyl-4,6-dioxo-2-trifluoromethyl-cyclohexanecarboxylic acid methyl ester that remains behind is esterified in the presence of 9.1 g of sodium hydroxide in a mixture of methanol and water at boiling temperature. The mixture is then acidified with hydrochloric acid and extracted with fresh ethyl acetate. After recrystallisation (ethyl acetate), pure 5-methyl-5-trifluoromethyl-cyclohexane-1,3-dione having a melting point of 150-152° C. is obtained.

Workup

  1. temperaturethe mixture is heated
  2. customfor 18 hours
  3. extractionAfter extraction with dilute hydrochloric acid
  4. concentrationagainst ethyl acetate, concentration
  5. customby evaporation
  6. additionThe non-purified 2-methyl-4,6-dioxo-2-trifluoromethyl-cyclohexanecarboxylic acid methyl ester that remains behind is esterified in the presence of 9.1 g of sodium hydroxide in a mixture of methanol and water
  7. extractionextracted with fresh ethyl acetate
  8. customAfter recrystallisation (ethyl acetate), pure 5-methyl-5-trifluoromethyl-cyclohexane-1,3-dione having a melting point of 150-152° C.
  9. customis obtained

Sources & evidence

ORD record
ord-f4efd0d6ab904100b8ededd088e7c2e2
Source dataset
uspto-grants-2005_05
Patent number
US06890885B2

Reaction notes

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