5-Hydroxy-2-nitrobenzoic acid → Methyl 5-hydroxy-2-nitrobenzoate
Reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH2:14](OC(=O)C1C=C(OCCOC)C(OCCOC)=CC=1N)C.S(Cl)(Cl)=O.C(=O)([O-])O.[Na+]>CO>[CH3:14][O:8][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([OH:1])[CH:3]=[CH:4][C:5]=1[N+:11]([O-:13])=[O:12]Participants
6
Conditions
- Temperature
- 80 °C
Procedure
5-Hydroxy-2-nitro-benzoic acid (compound A′) (1.5 g) was dissolved in methanol (15 ml). Thionyl chloride (1.5 ml) was added dropwise to the solution on an ice bath, and the mixture was then stirred at 80° C. for 12 hr. After the completion of the reaction, the reaction solution was neutralized with a saturated aqueous sodium hydrogencarbonate solution, and was then subjected to separatory extraction with ethyl acetate. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure to give crude 5-hydroxy-2-nitro-benzoic acid methyl ester (1.1 g, crude yield 70%).
Workup
- customAfter the completion of the reaction
- extractionwas then subjected to separatory extraction with ethyl acetate
- washThe organic layer was washed with saturated brine
- dry with materialwas dried over sodium sulfate
- concentrationwas then concentrated under the reduced pressure
Sources & evidence
- ORD record
- ord-ee036beac7ab423fac604c9c52e44916
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08134015B2
Reaction notes
Loading…