Hydrochloric Acid → HCID 18997599, compound

HRID 374623Notes

Reaction equation

HRID 374623 reaction equation
[F:1][C:2]([F:10])([F:9])[C:3]([CH3:8])=[CH:4][C:5](=[O:7])[CH3:6].[C:11](OCC)(=O)[CH2:12]C(C)=O.[O-][CH2:21]C.[Na+].Cl>O.C1C=CC=CC=1>[CH3:11][C:12]1[CH2:8][C:3]([CH3:21])([C:2]([F:10])([F:9])[F:1])[CH2:4][C:5](=[O:7])[CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8868Ethyl AcetoacetateHCID 2723922Sodium ethoxideHCID 54046664HCID 54046664, compound

Product 1

HCID 18997599HCID 18997599, compoundYield 116.6%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

In a dried 100 ml 3-neck flask, 15.2 g(0.1 mole) of 4-trifluoromethyl-3-penten-2-one prepared in Example 2, 13 g(0.1 mole)of ethyl acetoacetate and 3.4 g of sodium ethoxide were added to 60 ml of benzene, and stirred for 4 hrs at 60° C. The reaction mixture was cooled to room temperature and water was added. After neutralization using 10N hydrochloric acid solution, the organic layer was extracted, and dried over magnesium sulfate. The residue was distilled under the vacuum pressure of 1 mmHg, to obtain 11.2 g of the title compound as main product(yield: 58.3%) and 4.5 g of 4-ethoxycarbonyl-3,5-dimethyl-5-trifluoromethyl-2-cyclohexen-1-one(A-2) as by-product(yield: 17%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionthe organic layer was extracted
  3. dry with materialdried over magnesium sulfate
  4. distillationThe residue was distilled under the vacuum pressure of 1 mmHg

Sources & evidence

ORD record
ord-391996cae3654fdb85a82881b315b0c9
Source dataset
uspto-grants-1996_01
Patent number
US05481034

Reaction notes

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