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

HRID 612029Notes

Reaction equation

HRID 612029 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH2:13][CH2:14][CH2:15][Cl:16])=[CH:6][CH:5]=1.[N+:18]([O-])([OH:20])=[O:19]>C(O)(=O)C>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH2:13][CH2:14][CH2:15][Cl:16])=[CH:6][C:5]=1[N+:18]([O-:20])=[O:19]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 14407173Methyl 4-(3-chloropropoxy)-3-methoxybenzoate

Product 1

HCID 23032992Methyl 4-(3-chloropropoxy)-5-methoxy-2-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 100 g (386.5 mmol) 4(3-chloro-propoxy)-5-methoxy -benzoic acid methyl ester in 300 ml acetic acid was added dropwise 100 ml of 70% nitric acid. The mixture was heated to 50° C. for 1 hr and then poured into ice water. The mixture was extracted with chloroform. The organic solution was washed with dilute sodium hydroxide and then dried over magnesium sulfate. The solvent was removed. Ether was added an the mixture was stirred until solid was deposited. The solid was collected by filtration giving 98 g of 4-(3-Chloro-propoxy)-5-methoxy-2-nitro-benzoic acid methyl ester as white crystals: mass spectrum (electrospray, m/e,): M+H 303.8; 2M+NH4 623.9.

Workup

  1. extractionThe mixture was extracted with chloroform
  2. washThe organic solution was washed with dilute sodium hydroxide
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed
  5. additionEther was added an the mixture
  6. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-e1bff0617fb24c58a3f992285d451bc3
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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