Sodium Hydroxide → 2-(3-Methoxypropoxy)benzoic acid
Reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:19])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH2:14][CH2:15][CH2:16][O:17][CH3:18])C>C(O)C.O>[CH3:18][O:17][CH2:16][CH2:15][CH2:14][O:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[C:6]([OH:19])=[O:5]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
1N sodium hydroxide solution (11.1 ml) is added to a solution of 2-(3-methoxypropoxy)-benzoic acid ethyl ester (2.4 g) in ethanol (20 ml) and water (10 ml), and the reaction mixture is stirred at 50° C. for 7 hours. The mixture is concentrated and the acidified aqueous phase is extracted with dichloremethane (3×40 ml). The organic phase is washed with saturated sodium chloride solution, dried over magnesium sulfate and concentrated. 2-(3-Methoxypropoxy)-benzoic acid, Rf (hexane-ethyl acetate-glacial acetic acid 1:2:0.1)=0.43, is obtained in the form of a yellowish oil.
Workup
- concentrationThe mixture is concentrated
- extractionthe acidified aqueous phase is extracted with dichloremethane (3×40 ml)
- washThe organic phase is washed with saturated sodium chloride solution
- dry with materialdried over magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-50590508e3a143ad86bbeef666a3d3d2
- Source dataset
- uspto-grants-1997_06
- Patent number
- US05641778
Reaction notes
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