Sodium Hydroxide → HCID 59175214, compound

HRID 1929619Notes

Reaction equation

HRID 1929619 reaction equation
C([O:5][C:6](=[O:18])[CH2:7][CH2:8][C:9]1[CH:14]=[C:13]([F:15])[C:12]([CH3:16])=[C:11]([F:17])[CH:10]=1)CCC.[OH-].[Na+]>CO.O>[F:15][C:13]1[CH:14]=[C:9]([CH2:8][CH2:7][C:6]([OH:18])=[O:5])[CH:10]=[C:11]([F:17])[C:12]=1[CH3:16]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 66733858HCID 66733858, compound

Product 1

HCID 59175214HCID 59175214, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 3-(3,5-difluoro-4-methyl-phenyl)-propionic acid butyl ester (6.960 g; 27.157 mmol) in MeOH (150 ml) and water (25 ml) was added at rt aq. 1N NaOH (68 ml; 68 mmol). The resulting solution was further stirred at rt for 1 h. MeOH was then removed under reduced pressure. Water (25 ml) was added, and the mixture was acidified with aq. 1N HCl (68 ml) in order to reach pH=2. DCM (150 ml) was added, and the layers were shaken and separated. The aq. layer was further extracted with DCM (50 ml). The mixed organic layers were dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. The product 3-(3,5-difluoro-4-methyl-phenyl)-propionic acid was obtained as a pale yellow solid which was further dried under HV (5.090 g; 94%). LC-MS: tR=0.86 min.; [M+H]+: no ionisation.

Workup

  1. customMeOH was then removed under reduced pressure
  2. additionWater (25 ml) was added
  3. additionDCM (150 ml) was added
  4. stirringthe layers were shaken
  5. customseparated
  6. extractionThe aq. layer was further extracted with DCM (50 ml)
  7. dry with materialThe mixed organic layers were dried over anh. MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-5ba253d7276d4b888de220bf0a4ef2fa
Source dataset
uspto-grants-2012_05
Patent number
US08188082B2

Reaction notes

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