Potassium Hydroxide → HCID 57685593, compound

HRID 2078178Notes

Reaction equation

HRID 2078178 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:14])([CH3:13])[C:9]([O:11]C)=[O:10])=[C:4]([F:15])[CH:3]=1.[OH-].[K+]>CCO.C(OCC)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:13])([CH3:14])[C:9]([OH:11])=[O:10])=[C:4]([F:15])[CH:3]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 67100077HCID 67100077, compound

Product 1

HCID 57685593HCID 57685593, compoundYield 84.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
120 °C

Procedure

Methyl 2-(4-chloro-2-fluorophenyl)-2-methylpropanoate (8.11 g, 35.2 mmol) was dissolved in EtOH (70.3 mL) in a vial. KOH (3.95 g, 70.3 mmol) was added, and the sealed vial was heated at 120° C. for 2 hours. The reaction mixture was then diluted with 75 mL of diethyl ether, added to a separatory funnel, partitioned with water, washed with 75 mL of water, and separated. The aqueous layer was acidified to pH=3 with 3N HCl and extracted 2 times with 100 mL of diethyl ether. The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound (6.46 g) as a light yellow solid. MS (m/z)=217 (M+H)+.

Workup

  1. additionadded to a separatory funnel
  2. custompartitioned with water
  3. washwashed with 75 mL of water
  4. customseparated
  5. extractionextracted 2 times with 100 mL of diethyl ether
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e6fdc17db24744ccac7cb3f9673efe23
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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