Acetic Acid → HCID 22466721, compound

HRID 384803Notes

Reaction equation

HRID 384803 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][C:7]=1[O:15][CH3:16].[N:17]([O-:19])=[O:18].[Na+].C(O)(=O)C.[N+]([O-])(O)=O>O>[CH3:16][O:15][C:7]1[C:6]([O:5][CH2:4][CH2:3][CH2:2][Cl:1])=[CH:14][C:13]([N+:17]([O-:19])=[O:18])=[C:9]([CH:8]=1)[C:10]([OH:12])=[O:11]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 944Nitric AcidHCID 10354496Benzoic acid, 4-(3-chloropropoxy)-3-methoxy-HCID 23668193Sodium Nitrite

Product 1

HCID 22466721HCID 22466721, compoundYield 944.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

In a 50 mL volume glass flask equipped with a stirrer, a thermometer and a dropping funnel were placed 16.2 g (65.4 mmol) of 4-(3-chloropropoxy)-3-methoxybenzoic acid (purity: 98%) obtained in Reference Example III-7, 0.45 g (6.54 mmol) of sodium nitrite, and 20 mL of acetic acid. The resulting mixture was heated to 40° C. under stirring. To the reaction mixture was dropwise added slowly 27.6 g (262.0 mmol) of nitric acid (60 wt. %), and the mixture was heated 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 with 30 mL of water, and dried under reduced pressure, to give 17.9 g (isolated yield: 93.0%, purity: 99% in terms of area percentage determined by high performance liquid chromatography) of 5-methoxy-4-(3-chloropropoxy)-2-nitrobenzoic acid as a white crystalline product.

Workup

  1. customIn a 50 mL volume glass flask equipped with a stirrer
  2. temperaturethe mixture was heated at the same temperature for 5 hours
  3. temperaturethe aqueous mixture was cooled to 20° C.
  4. customprecipitating a crystalline product
  5. filtrationThe crystalline product was collected by filtration
  6. washwashed with 30 mL of water
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-7cdd8f1e548a4e3bb3bf9d03d150245a
Source dataset
uspto-grants-2013_02
Patent number
US08367824B2

Reaction notes

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