Acetic Acid → Methyl 4-(3-chloropropoxy)-5-methoxy-2-nitrobenzoate

HRID 384771Notes

Reaction equation

HRID 384771 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>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:7]([O:16][CH3:17])=[CH:8][C:9]([C:10]([O:12][CH3:13])=[O:11])=[C:14]([N+:18]([O-:20])=[O:19])[CH:15]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 944Nitric AcidHCID 14407173Methyl 4-(3-chloropropoxy)-3-methoxybenzoateHCID 23668193Sodium Nitrite

Product 1

HCID 23032992Methyl 4-(3-chloropropoxy)-5-methoxy-2-nitrobenzoateYield 96.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

In a 100 mL volume glass flask equipped with a stirrer, a thermometer and a dropping funnel were placed 14.0 of the above-obtained solution mainly containing methyl 4-(3-chloropropoxy)-3-methoxybenzoate, 0.20 g (2.60 mmol) of sodium nitrite, and 17.5 mL of acetic acid. The resulting mixture was heated to 40-50° C. under stirring. To the reaction mixture was dropwise added slowly 22.4 g (215.2 mmol) of nitric acid (60 wt. %), and the mixture was kept at the same temperature for 2 hours. After the reaction was complete, 42 mL of water was added to the reaction mixture. Then, the organic portion was separated and washed with warm water. Analysis of the organic portion by high performance liquid chromatography (absolute quantitative analysis) indicated that 15.7 g (reaction yield: 96.2%) of methyl 4-(3-chloropropoxy)-5-methoxy-2-nitrobenzoate was produced.

Workup

  1. customIn a 100 mL volume glass flask equipped with a stirrer
  2. customThen, the organic portion was separated
  3. washwashed with warm water

Sources & evidence

ORD record
ord-f0a2aaaad8004cedae3736074c00588e
Source dataset
uspto-grants-2013_02
Patent number
US08367824B2

Reaction notes

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