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

HRID 384772Notes

Reaction equation

HRID 384772 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 94.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

In a 500 mL volume glass flask equipped with a stirrer, a thermometer and a dropping funnel were placed 138.0 of the solution mainly containing methyl 4-(3-chloropropoxy)-3-methoxybenzoate, 0.93 g (13.7 mmol) of sodium nitrite, and 90 mL of acetic acid. The resulting mixture was heated to 40-50° C. under stirring. To the reaction mixture was dropwise added slowly 111.5 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, 210 mL of water was added to the reaction mixture. Then, the organic portion was separated and washed with 210 mL of warm water. Analysis of the organic portion by high performance liquid chromatography (absolute quantitative analysis) indicated that 78.7 g (reaction yield: 94.5%) of methyl 4-(3-chloropropoxy)-5-methoxy-2-nitrobenzoate was produced.

Workup

  1. customIn a 500 mL volume glass flask equipped with a stirrer
  2. customThen, the organic portion was separated
  3. washwashed with 210 mL of warm water

Sources & evidence

ORD record
ord-cf9dc465debf4ae38d00f93c036e3be8
Source dataset
uspto-grants-2013_02
Patent number
US08367824B2

Reaction notes

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