Potassium Carbonate → Methyl 3-hydroxy-2-{[2-(methyloxy)ethyl]oxy}-5-nitrobenzoate
Reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[C:15]([O:16]C(C2C=CC=CC=2)=O)=[CH:14][C:13]([N+:25]([O-:27])=[O:26])=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9].C(=O)([O-])[O-].[K+].[K+]>CO>[OH:16][C:15]1[C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])=[C:7]([CH:12]=[C:13]([N+:25]([O-:27])=[O:26])[CH:14]=1)[C:8]([O:10][CH3:11])=[O:9]Participants
Procedure
Methyl 2-{[2-(methyloxy)ethyl]oxy}-5-nitro-3-[(phenylcarbonyl)oxy]benzoate (8.1 g, 21.6 mmol) was dissolved in methanol (150 mL) followed by the addition of potassium carbonate (3.3 g, 24 mmol). The reaction mixture was stirred at room temperature for one hour, filtered and then acidified with 4N hydrogen chloride in dioxane. It was concentrated and then re-dissolved in ethyl acetate (100 mL), washed with water and brine (100 mL each), dried over sodium sulfate, filtered and concentrated to give an oily residue which was purified by flash chromatography (silica gel, 30% ethyl acetate-hexane) to provide methyl 3-hydroxy-2-{[2-(methyloxy)ethyl]oxy}-5-nitrobenzoate (8.1 g, 21.0 mmol, 97% yield). 1H NMR (400 MHz, CDCl3): 8.69 (s, 1H), 8.24-8.23 (d, 1H), 7.95-7.94 (d, 1H), 4.31-4.29 (m, 2H), 3.95 (s, 3H), 3.79-3.77 (m, 2H), 3.58 (s, 3H).
Workup
- filtrationfiltered
- concentrationIt was concentrated
- dissolutionre-dissolved in ethyl acetate (100 mL)
- washwashed with water and brine (100 mL each)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customto give an oily residue which
- customwas purified by flash chromatography (silica gel, 30% ethyl acetate-hexane)
Sources & evidence
- ORD record
- ord-1a0c5ae894ec46ebadca86fc4b7d47dc
- Source dataset
- uspto-grants-2011_01
- Patent number
- US07872014B2
Reaction notes
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