Hydrochloric Acid → HCID 68194187, compound

HRID 2405150Notes

Reaction equation

HRID 2405150 reaction equation
C([O:3][C:4](=[O:19])[C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:18])([F:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7][CH:6]=1)C.C([O-])([O-])=O.[K+].[K+].Cl>>[CH2:15]([O:14][C:12](=[O:13])[C:11]([C:8]1[CH:9]=[CH:10][C:5]([C:4]([OH:19])=[O:3])=[CH:6][CH:7]=1)([F:17])[F:18])[CH3:16]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 53375273HCID 53375273, compound2×

Product 1

HCID 68194187HCID 68194187, compound

Procedure

According to the above-described scheme, 4-(2-ethoxy-1,1-difluoro-2-oxoethyl)benzoic acid ethyl ester (Compound 2d; 108.9 mg, 0.4 mmol) and 1N K2CO3 solution (1.5 mL) were put into an eggplant flask, and the mixture was stirred at room temperature for 26 hours. After the reaction, the reaction mixture was neutralized with 5% HCl solution, extracted with ethyl acetate and washed with water, and an organic layer was dried with anhydrous sodium sulfate. Ethyl acetate was distilled away under reduced pressure, and by carrying out purification by silica gel column chromatography, 4-(2-ethoxy-1,1-difluoro-2-oxoethyl)benzoic acid (Compound 4d) was obtained with a yield of 86%.

Workup

  1. customwere put into an eggplant flask
  2. customAfter the reaction
  3. extractionextracted with ethyl acetate
  4. washwashed with water
  5. dry with materialan organic layer was dried with anhydrous sodium sulfate
  6. distillationEthyl acetate was distilled away under reduced pressure
  7. custompurification by silica gel column chromatography

Sources & evidence

ORD record
ord-e12c1d0f090c4391855adb5fc4d603a6
Source dataset
uspto-grants-2014_08
Patent number
US08802886B2

Reaction notes

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