Hydrochloric Acid → 3-[4-[2-(N-dodecyl-N-methylamino)ethoxy]phenyl]propanoic acid
Reaction equation
C[O:2][C:3](=[O:29])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][N:15]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH3:16])=[CH:8][CH:7]=1.[OH-].[K+].O.Cl>C(O)C>[CH2:17]([N:15]([CH2:14][CH2:13][O:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][C:3]([OH:29])=[O:2])=[CH:7][CH:8]=1)[CH3:16])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 22 °C
Procedure
A solution of 3-[4-[2-(N-dodecyl-N-methylamino)ethoxy]phenyl]propanoic acid methyl ester (2.30 g, 5.69 mmol) in ethanol (25 ml) was treated with potassium hydroxide (0.64 g, 11.4 mmol) and water (5 ml) and stirred at 22° C. for 2 h. The reaction mixture was then acidified to pH 4 with 1M hydrochloric acid and extracted twice with ethyl acetate. The combined extracts were washed with brine, dried (MgSO4) and evaporated under reduced pressure to give a white solid. Recrystallization from ethyl acetate gave 2.20 g (89%) of 3-[4-[2-(N-dodecyl-N-methylamino)ethoxy]phenyl]propanoic acid as white crystals.
Workup
- extractionextracted twice with ethyl acetate
- washThe combined extracts were washed with brine
- dry with materialdried (MgSO4)
- customevaporated under reduced pressure
- customto give a white solid
- customRecrystallization from ethyl acetate
Sources & evidence
- ORD record
- ord-6a0dace1d0cc41cc84fe8260ebf64e91
- Source dataset
- uspto-grants-2002_02
- Patent number
- US06350892B1
Reaction notes
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