Nitric Acid → 5-Formyl-2-hydroxy-3-nitrobenzoic acid

HRID 401186Notes

Reaction equation

HRID 401186 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([OH:12])=[C:7]([CH:11]=1)[C:8]([OH:10])=[O:9])=[O:2].[N+:13]([O-])([OH:15])=[O:14]>S(=O)(=O)(O)O>[CH:1]([C:3]1[CH:4]=[C:5]([N+:13]([O-:15])=[O:14])[C:6]([OH:12])=[C:7]([CH:11]=1)[C:8]([OH:10])=[O:9])=[O:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 692265-Formylsalicylic acid

Product 1

HCID 866693375-Formyl-2-hydroxy-3-nitrobenzoic acidYield 86.6%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 5-formyl-2-hydroxybenzoic acid (2 g, 12.04 mmol) in concentrated sulfuric acid (5 mL) was added a mixture of concentrated nitric acid (1 mL) and concentrated sulfuric acid (1 mL) at 0° C. The resulting suspension was stirred at 0° C. for 3 h, and poured into ice water (30 mL). The solid was collected by filtration, washed with water (30 mL), and dried in vacuo to give Intermediate 55 (2.2 g, yield 86.6%).

Workup

  1. filtrationThe solid was collected by filtration
  2. washwashed with water (30 mL)
  3. customdried in vacuo

Sources & evidence

ORD record
ord-cc1ce73712ef48bebf0955e9ffe6c17d
Source dataset
uspto-grants-2014_06
Patent number
US08741915B2

Reaction notes

Loading…