Acetic Acid → Methyl 4-(3-chloropropoxy)-5-methoxy-2-nitrobenzoate
Reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][C:7]=1[O:16][CH3:17].[N:18]([O-:20])=[O:19].[Na+].C(O)(=O)C.[N+]([O-])(O)=O>O>[CH3:17][O:16][C:7]1[C:6]([O:5][CH2:4][CH2:3][CH2:2][Cl:1])=[CH:15][C:14]([N+:18]([O-:20])=[O:19])=[C:9]([CH:8]=1)[C:10]([O:12][CH3:13])=[O:11]Participants
Conditions
- Temperature
- 40 °C
Procedure
In a 100 mL volume glass flask equipped with a stirrer, a thermometer and a dropping funnel were placed 10.1 g (38.7 mmol) of methyl 4-(3-chloropropoxy)-3-methoxybenzoate (purity: 99%) obtained in Reference Example III-3, 0.27 g (3.87 mmol) of sodium nitrite, and 12.5 mL of acetic acid. The resulting mixture was heated to 40° C. under stirring. To the reaction mixture was dropwise added slowly 16.2 g (154.8 mmol) of nitric acid (60 wt. %), and the mixture was kept at the same temperature for 5 hours. After the reaction was complete, 20 mL of water was added to the reaction mixture, and the aqueous mixture was cooled to 20° C., precipitating a crystalline product. The crystalline product was collected by filtration, washed successively with 30 mL of water and 30 mL of n-heptane, and dried under reduced pressure, to give 10.9 g (isolated yield: 92.0%, purity: 98% in terms of area percentage determined by high performance liquid chromatography) of methyl 5-methoxy-4-(3-chloropropoxy)-2-nitrobenzoate as a white crystalline product.
Workup
- customIn a 100 mL volume glass flask equipped with a stirrer
- temperaturethe aqueous mixture was cooled to 20° C.
- customprecipitating a crystalline product
- filtrationThe crystalline product was collected by filtration
- washwashed successively with 30 mL of water and 30 mL of n-heptane
- customdried under reduced pressure
Sources & evidence
- ORD record
- ord-f5b07123cf6242adac189c863b2606f2
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08367824B2
Reaction notes
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