Water → 4-(4-Methoxyphenyl)-4-oxo-3-phenylbutanoic acid

HRID 1186841Notes

Reaction equation

HRID 1186841 reaction equation
C([O:3][C:4](=[O:23])[CH2:5][CH:6]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:7]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)=[O:8])C.O.[OH-].[Na+]>CCO>[CH3:16][O:15][C:12]1[CH:11]=[CH:10][C:9]([C:7](=[O:8])[CH:6]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:5][C:4]([OH:23])=[O:3])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 134415094-(4-Methoxy-phenyl)-4-oxo-3-phenyl-butyric acid ethyl ester

Product 1

HCID 43613644-(4-Methoxyphenyl)-4-oxo-3-phenylbutanoic acidYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-(4-methoxy-phenyl)-4-oxo-3-phenyl-butyric acid ethyl ester (5.0 g, 16 mmol) in EtOH:H2O (60 mL 1:1) was stirred as 10N NaOH (16 mL) was added dropwise. The reaction was stirred at rt for 1 hr. The solvent was evaporated and the residue was diluted with water (50 mL) and extracted with CH2Cl2 (2×20 mL). The aqueous layer was then acidified with 3N HCl to pH ˜2-3, extracted with CH2Cl2 (3×30 mL). The CH2Cl2 extracts were dried over MgSO4, and the oil was crystallized from Et2O/MeOH to give 4.5 g (99%) of 4-(4-methoxy-phenyl)-4-oxo-3-phenyl-butyric acid: mp 157-9° C.; MS m/z 283 (M−H).

Workup

  1. additionwas added dropwise
  2. customThe solvent was evaporated
  3. additionthe residue was diluted with water (50 mL)
  4. extractionextracted with CH2Cl2 (2×20 mL)
  5. extractionextracted with CH2Cl2 (3×30 mL)
  6. dry with materialThe CH2Cl2 extracts were dried over MgSO4
  7. customthe oil was crystallized from Et2O/MeOH

Sources & evidence

ORD record
ord-358cfa7d114f413186b0b3d726a610d6
Source dataset
uspto-grants-2014_03
Patent number
US08673916B2

Reaction notes

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