Hydrochloric Acid → HCID 23568091, compound

HRID 2405151Notes

Reaction equation

HRID 2405151 reaction equation
C([O:3][C:4](=[O:17])[C:5]([C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:16])[CH3:15])=[CH:10][CH:9]=1)([F:7])[F:6])C.[OH-].[Na+].Cl>>[C:14]([C:11]1[CH:10]=[CH:9][C:8]([C:5]([F:6])([F:7])[C:4]([OH:17])=[O:3])=[CH:13][CH:12]=1)(=[O:16])[CH3:15]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68193922HCID 68193922, compound2×

Product 1

HCID 23568091HCID 23568091, compound

Conditions

Temperature
100 °C

Procedure

According to the above-described scheme, 2-(4-acetylphenyl)-2,2-difluoroacetic acid ethyl ester (Compound 2e; 436.0 mg, 1.8 mmol) and 1N NaOH solution (3.0 mL) were put into an eggplant flask, and the mixture was stirred at 100° C. for 1.5 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, 2-(4-acetylphenyl)-2,2-difluoroacetic acid (Compound 4e) was obtained with a yield of 96%.

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-30095e8527c74ed886c8c98be39ef369
Source dataset
uspto-grants-2014_08
Patent number
US08802886B2

Reaction notes

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