Hydrochloric Acid → Methyl 5-methyl-2-nitrobenzoate
Reaction equation
[CH3:1][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].[C:14](=O)([O-])[O-].[K+].[K+].CI.Cl>CN(C)C=O.O>[CH3:14][O:8][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([CH3:1])[CH:3]=[CH:4][C:5]=1[N+:11]([O-:13])=[O:12]Participants
7
Procedure
There was dissolved, in 200 mL of N,N-dimethylformamide, 20.0 g of 5-methyl-2-nitrobenzoic acid, 22.9 g of potassium carbonate and then 8.2 mL of methyl iodide were added to the resulting solution and the mixture was stirred at room temperature for 4 hours. To the reaction liquid, there were added 400 mL of water and 200 mL of a 1M hydrochloric acid solution, then extracted with 900 mL of ethyl acetate, the extract was washed with 200 mL of a saturated sodium hydrogen carbonate solution and 200 mL of a saturated common salt solution and the solvent was then distilled off under reduced pressure to thus give 20.6 g of the title compound as a crude product.
Workup
- customTo the reaction liquid, there
- extractionextracted with 900 mL of ethyl acetate
- washthe extract was washed with 200 mL of a saturated sodium hydrogen carbonate solution and 200 mL of a saturated common salt solution
- distillationthe solvent was then distilled off under reduced pressure to thus give 20.6 g of the title compound as a crude product
Sources & evidence
- ORD record
- ord-167c26b2eeca460986d079af12bcf123
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08546610B2
Reaction notes
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