Methanol → 2-[5-(4-Chlorophenyl)-2-ethylphenyl]-2-oxoacetic acid

HRID 579268Notes

Reaction equation

HRID 579268 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([CH2:21][CH3:22])=[C:12]([C:14](=[O:20])[C:15]([O:17]CC)=[O:16])[CH:13]=2)=[CH:4][CH:3]=1.CO.[OH-].[K+].CCCCCC>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([CH2:21][CH3:22])=[C:12]([C:14](=[O:20])[C:15]([OH:17])=[O:16])[CH:13]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 887Methanol2×HCID 8058HexaneHCID 14797Potassium Hydroxide2×HCID 66691355Ethyl 2-[5-(4-chlorophenyl)-2-ethylphenyl]-2-oxoacetate

Product 1

HCID 666915552-[5-(4-Chlorophenyl)-2-ethylphenyl]-2-oxoacetic acidYield 82.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a 50 ml volume three-necked flask, ethyl 2-[5-(4-chlorophenyl)-2-ethylphenyl]-2-oxoacetate (9-c) (1.43 g), methanol (1.9 ml), and potassium hydroxide (600 mg) dissolved in water (3 ml) were added at room temperature, then added methanol (7.6 ml) and water (3 ml), and stirred at 40° C. for 2 hours. To the mixture was added hexane and 2N aqueous potassium hydroxide solution (3 ml), and then the layers were separated. The aqueous layer was washed with hexane again. The organic layers were combined, and extracted with 2N potassium hydroxide. To the resulting aqueous layer, 10 w/w % of hydrochloric acid was added to adjust pH to less than 1, and extracted with ethyl acetate 3 times. The organic layers were combined, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give 1.081 g of 2-[5-(4-chlorophenyl)-2-ethylphenyl]-2-oxoacetic acid (8-c).

Workup

  1. additionwere added at room temperature
  2. customthe layers were separated
  3. washThe aqueous layer was washed with hexane again
  4. extractionextracted with 2N potassium hydroxide
  5. additionTo the resulting aqueous layer, 10 w/w % of hydrochloric acid was added
  6. extractionextracted with ethyl acetate 3 times
  7. washwashed with saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-abdd945371134654988ab557bd3f3132
Source dataset
uspto-grants-2015_05
Patent number
US09040709B2

Reaction notes

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