Potassium Hydroxide → HCID 67099989, compound

HRID 1868873Notes

Reaction equation

HRID 1868873 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])=[CH:4][C:3]=1[F:15].[OH-].[K+]>CCO.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:13])([CH3:14])[C:9]([OH:11])=[O:10])=[CH:4][C:3]=1[F:15]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 67099743Methyl 4-chloro-3-fluoro-α,α-dimethylbenzeneacetate

Product 1

HCID 67099989HCID 67099989, compoundYield 95.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of methyl 2-(4-chloro-3-fluorophenyl)-2-methylpropanoate (2.94 g, 12.7 mmol) and KOH (7.15 g, 127 mmol) in EtOH (90 mL) and water (30 mL) was stirred at 150° C. in a sealed vessel for 3 hours. The solution was concentrated in vacuo, diluted with 10% HCl (aq) (150 mL), and extracted with EtOAc (2×100 mL). The combined organic layers were washed with water (2×100 mL) and then with brine (75 mL). The organic layer was dried over MgSO4, concentrated, and dried in vacuo to give 2-(4-chloro-3-fluorophenyl)-2-methylpropanoic acid (2.63 g). MS m/e=217.3 (M+H)+.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. additiondiluted with 10% HCl (aq) (150 mL)
  3. extractionextracted with EtOAc (2×100 mL)
  4. washThe combined organic layers were washed with water (2×100 mL)
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated
  7. customdried in vacuo

Sources & evidence

ORD record
ord-d43e1b1ba97a43268c7c10912f6a301c
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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