Nitric Acid → HCID 68458934, compound

HRID 506252Notes

Reaction equation

HRID 506252 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:12])[C:5](=[CH:10][CH:11]=1)[C:6]([O:8][CH3:9])=[O:7].S(=O)(=O)(O)O.[N+:18]([O-])([OH:20])=[O:19]>>[Cl:1][C:2]1[C:3]([N+:18]([O-:20])=[O:19])=[C:4]([OH:12])[C:5](=[CH:10][CH:11]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 327085Methyl 4-chloro-2-hydroxybenzoate

Product 1

HCID 68458934HCID 68458934, compoundYield 52%

Conditions

Temperature
0 °C

Procedure

A 250-mL single-neck round bottomed flask equipped with a magnetic stirrer was charged with methyl 4-chlorosalicylate (25.0 g, 134 mmol) followed by concentrated sulfuric acid (73 mL) and the resulting suspension cooled to 0° C. using an ice bath. Concentrated nitric acid (6.20 mL, 147 mmol) was then added and the reaction stirred for 1 h at 0° C. After this time, the reaction was poured into ice and the resulting precipitate collected by vacuum filtration. The filter cake was washed with water (20 mL) and then re-crystallized from hot ethanol (100 mL) to afford methyl 4-chloro-3-nitrosalicylate in 52% yield (16.0 g) as white solid: 1H NMR (300 MHz, CDCl3) δ 8.15 (d, J=2.7 Hz, 1H), 8.11 (d, J=2.7 Hz, 1H), 4.03 (s, 3H); MS (ESI) m/z 232 [M+H]+.

Workup

  1. customA 250-mL single-neck round bottomed flask equipped with a magnetic stirrer
  2. additionAfter this time, the reaction was poured into ice
  3. filtrationthe resulting precipitate collected by vacuum filtration
  4. washThe filter cake was washed with water (20 mL)
  5. customre-crystallized from hot ethanol (100 mL)

Sources & evidence

ORD record
ord-807209fd73f445b4a04d43180c800e55
Source dataset
uspto-grants-2010_08
Patent number
US07781430B2

Reaction notes

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