Hydrochloric Acid → HCID 66618878, compound

HRID 406345Notes

Reaction equation

HRID 406345 reaction equation
[OH:1][C:2]1[CH2:7][CH2:6][C:5]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)([C:8]([O:10][CH3:11])=[O:9])[CH2:4][C:3]=1C(OC)=O.[OH-].[K+].C(OCC)(=O)C.Cl>C1COCC1.CO.O>[O:1]=[C:2]1[CH2:7][CH2:6][C:5]([C:12]2[CH:13]=[CH:14][C:15]([C:18]([F:19])([F:20])[F:21])=[CH:16][CH:17]=2)([C:8]([O:10][CH3:11])=[O:9])[CH2:4][CH2:3]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 66634001HCID 66634001, compound

Product 1

HCID 66618878HCID 66618878, compoundYield 28.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

Dimethyl 4-hydroxy-1-(4-trifluoromethylphenyl)-3-cyclohexene-1,3-dicarboxylate (1.13 g) was dissolved in a mixed solvent of THF (3 mL) and methanol (3 mL). A 1 N potassium hydroxide solution (1.89 mL) was added and the mixture was stirred at 100° C. for eight hours. After leaving to cool, ethyl acetate and water were added to the reaction solution, followed by neutralization with 1 N hydrochloric acid. The organic layer was separated, washed with brine and then dried over anhydrous sodium sulfate. The drying agent was separated by filtration and then the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (272 mg). The property values of the compound are as follows.

Workup

  1. customAfter leaving
  2. temperatureto cool
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe drying agent was separated by filtration
  7. concentrationthe organic layer was concentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-413f3ca8e25741e48892dc3cb70d8984
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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