Sodium Hydroxide → 2-Methoxymethoxy-3-n-propyl-4-methoxybenzoic acid
Reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[C:14]([CH2:15][CH2:16][CH3:17])=[C:13]([O:18][CH3:19])[CH:12]=[CH:11][C:6]=1[C:7]([O:9]C)=[O:8].[OH-].[Na+]>CO>[CH3:1][O:2][CH2:3][O:4][C:5]1[C:14]([CH2:15][CH2:16][CH3:17])=[C:13]([O:18][CH3:19])[CH:12]=[CH:11][C:6]=1[C:7]([OH:9])=[O:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
The methyl 2-methoxymethoxy-3-n-propyl-4-methoxybenzoate (31.9 g) was dissolved in methanol (280 ml), and 10% aqueous solution of sodium hydroxide (70 ml) was added thereto. The mixture was agitated at 60° C. for 4 hours and then at room temperature for another 80 hours. The reaction mixture was concentrated to about one third of the original volume in evacuated atomosphere, cooled to 0° C., acidified by adding 2N aqueous hydrochloric acid thereto, and then extracted twice with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated in evacuated atomosphere to produce 2-methoxymethoxy-3-n-propyl-4-methoxybenzoic acid (28.8 g).
Workup
- waitat room temperature for another 80 hours
- concentrationThe reaction mixture was concentrated to about one third of the original volume in evacuated atomosphere
- temperaturecooled to 0° C.
- additionby adding 2N aqueous hydrochloric acid
- extractionextracted twice with ethyl acetate
- washThe organic layer was washed with saturated aqueous solution of sodium chloride
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated in evacuated atomosphere
Sources & evidence
- ORD record
- ord-8940b44624e146c2b2fd0b20e7746833
- Source dataset
- uspto-grants-1992_10
- Patent number
- US05155106
Reaction notes
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