Water → 3-Formylchromone

HRID 866339

Reaction equation

HRID 866339 reaction equation
[OH:1][CH2:2][C:3]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][CH:4]=1.O>[N+]([O-])(O)=O>[CH:2]([C:3]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][CH:4]=1)=[O:1]

Participants

4

Reactant 2

HCID 962WaterHCID 113557983-(hydroxymethyl)-4H-chromen-4-one

Product 1

HCID 871123-Formylchromone

Reagents, catalysts & solvents 1

HCID 944Nitric AcidSolvent

Conditions

Temperature
25 °C

Procedure

A quantity of 35.2 g. (0.2 mole) of 3-(hydroxymethyl)chromone is dissolved in 250 ml of concentrated nitric acid with stirring at 25° C. There is no initial heat of reaction. The temperature gradually rises to 30° C over the next several minutes and is kept there for about five minutes with ice-acetone bath cooling. Water, 600 ml, is added to the reaction solution. The separated, pale yellow solid is filtered, washed well with water and dried to give 25 g. of crude aldehyde melting at 145°-148°.

Workup

  1. temperatureno initial heat of reaction
  2. customgradually rises to 30° C over the next several minutes
  3. temperaturecooling
  4. filtrationThe separated, pale yellow solid is filtered
  5. washwashed well with water
  6. customdried
  7. customto give 25 g

Sources & evidence

ORD record
ord-f9cb4f5f974a41769ac715fee52a55f0
Source dataset
uspto-grants-1978_07
Patent number
US04098799

Linked notes

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