Nitric Acid → 3-Tert-butyl-2-hydroxy-5-nitrobenzaldehyde

HRID 2121281Notes

Reaction equation

HRID 2121281 reaction equation
[C:1]([C:5]1[C:6]([OH:13])=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH:8]=[O:9])([CH3:4])([CH3:3])[CH3:2].[N+:14]([O-])([OH:16])=[O:15]>C(O)(=O)C>[C:1]([C:5]1[C:6]([OH:13])=[C:7]([CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=1)[CH:8]=[O:9])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 36786753-tert-Butyl-2-hydroxybenzaldehyde

Product 1

HCID 125220373-Tert-butyl-2-hydroxy-5-nitrobenzaldehydeYield 64%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5.0 g (28 mmol) of 3-tert-butyl-2-hydroxybenzaldehyde in 8 ml of glacial acetic acid were introduced into a 50 ml two-necked flask fitted with magnetic stirrer and dropping funnel, and 2.8 ml (68 mmol) of nitric acid were added at a temperature of below 5° C. The batch was subsequently stirred further at room temperature for one hour. The product was isolated by precipitation on ice and washed with water. After recyrstallization of the methanol, the product was dried. The yield was 64%.

Workup

  1. customfitted with magnetic stirrer
  2. customThe product was isolated by precipitation on ice
  3. washwashed with water
  4. dry with materialAfter recyrstallization of the methanol, the product was dried

Sources & evidence

ORD record
ord-190f415a09f143debf5e88e4e9187211
Source dataset
uspto-grants-2004_02
Patent number
US06695977B2

Reaction notes

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