Sodium Hydroxide → 4-(2',3'-Dimethoxyphenyl) 3-phenylbutyric acid
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
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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, filtered 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
- concentrationThe reaction mixture was concentrated
- customthe residue was partitioned between 300 mL of diethyl ether and 200 mL of water
- customThe layers were separated
- extractionextracted with 3×200 mL of diethyl ether
- washwashed with brine
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-dee47decf2594124a16bab6ee11d0feb
- Source dataset
- uspto-grants-1997_01
- Patent number
- US05591884
Reaction notes
Loading…