Nitric Acid → Methyl 2-{[2-(methyloxy)ethyl]oxy}-5-nitro-3-[(phenylcarbonyl)oxy]benzoate
Reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[C:15]([O:16][C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:18])=[CH:14][CH:13]=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9].[N+:25]([O-])([OH:27])=[O:26].S(=O)(=O)(O)O>ClCCl>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[C:15]([O:16][C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:18])=[CH:14][C:13]([N+:25]([O-:27])=[O:26])=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9]Participants
Procedure
Methyl 2-{[2-(methyloxy)ethyl]oxy}-3-[(phenylcarbonyl)oxy]benzoate (8.0 g, 24.2 mmol) was added drop wise over 15 minutes to a mixture of 90% nitric acid (15 mL) and concentrated sulfuric acid (3 mL) at −5° C. The resulting mixture was stirred for an additional 15 minutes then it was poured into a mixture of ice (200 g) and dichloromethane (200 mL). The organic portion was separated, washed with saturated sodium bicarbonate solution, brine (100 mL each) dried over sodium sulfate, filtered and concentrated to give methyl 2-{[2-(methyloxy)ethyl]oxy}-5-nitro-3-[(phenylcarbonyl)oxy]benzoate (8.1 g, 21.6 mmol, 89% yield). 1H NMR (400 MHz, CDCl3): 8.63-8.62 (d, 1H), 8.27-8.26 (d, 1H), 8.21-8.19 (m, 2H), 7.69-7.67 (d, d, 1H), 7.55-7.51 (d, d, 2H), 4.26-4.24 (m, 2H), 3.96 (s, 3H), 3.58-3.56 (m, 2H), 3.12 (s, 3H).
Workup
- customThe organic portion was separated
- washwashed with saturated sodium bicarbonate solution, brine (100 mL each)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-ad4c551602374a3aa6c30eb1bb2beb66
- Source dataset
- uspto-grants-2011_01
- Patent number
- US07872014B2
Reaction notes
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