Sodium Hydroxide → 4-(2',3'-Dimethoxyphenyl) 3-phenylbutyric acid

HRID 54120

Reaction equation

HRID 54120 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:11][CH:12]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:13][C:14]([O:16]CC)=[O:15].[OH-].[Na+]>CO>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:11][CH:12]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH2:13][C:14]([OH:16])=[O:15]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19961164Ethyl 4-(2',3'-dimethoxyphenyl)-3-phenylbutyrate

Product 1

HCID 124785434-(2',3'-Dimethoxyphenyl) 3-phenylbutyric acidYield 100.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 4-(2',3'-dimethoxyphenyl)-3-phenylbutyrate (40.3 g, 123 mmol), from Step 3, was dissolved in 400 mL of methanol and 62 mL of 3M aqueous sodium hydroxide solution was added in one portion. The reaction mixture was stirred at ambient temperature for 18 h. The reaction mixture was concentrated and the residue was partitioned between 300 mL of diethyl ether and 200 mL of water. The layers were separated and the aqueous layer was adjusted to pH 6 with 6M aqueous hydrochloric acid solution and extracted with 3×200 mL of diethyl ether. The organic layers were combined, washed with brine, dried over anhydrous magnesium sulfate, faltered and concentrated in vacuo to give 37 g (100% yield) of the title compound as a colorless oil. The 1H NMR spectrum was identical to the spectrum reported for the product of Step 5 of Method A, Example 1.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was partitioned between 300 mL of diethyl ether and 200 mL of water
  3. customThe layers were separated
  4. extractionextracted with 3×200 mL of diethyl ether
  5. washwashed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-977908a01ff54d448822db6a60e9a34a
Source dataset
uspto-grants-1997_04
Patent number
US05621133

Linked notes

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