Methanol → Benzoic acid, 4-hydroxy-3-nitro-, methyl ester
Reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].CO.S(=O)(=O)(O)O.[C:21](=O)([O-])O.[Na+]>ClCCCl>[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:21])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]Participants
6
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 4-hydroxy-3-nitrobenzoic acid (15.8 g, 86.3 mmol) in 1,2-dichloroethane (150 mL) were added methanol (14 mL) and conc. sulfuric acid (0.5 mL) and the mixture was heated to 80° C. and stirred. Methanol (9 mL) was added on the way and the mixture was stirred for 21 hours. The reaction mixture was added to a saturated aqueous sodium hydrogencarbonate solution (400 mL) and extracted with chloroform. The extract was washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure to give methyl 4-hydroxy-3-nitrobenzoate as a yellow solid (11.5 g, 68%).
Workup
- stirringthe mixture was stirred for 21 hours
- extractionextracted with chloroform
- washThe extract was washed with saturated brine
- dry with materialdried over magnesium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-fdc5f33887bf4b0eb3cae6a0a7759066
- Source dataset
- uspto-grants-2000_06
- Patent number
- US06080738
Reaction notes
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