ChemicalBook CAS DataBase List 4,6-Dihydroxy-2,3-dimethylbenzaldehyde

4,6-Dihydroxy-2,3-dimethylbenzaldehyde synthesis

4synthesis methods

Product Name:4,6-Dihydroxy-2,3-dimethylbenzaldehyde
CAS Number:2990-31-0
Molecular formula:
Molecular Weight:0

527-55-9
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2990-31-0
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Yield:2990-31-0 71%

Reaction Conditions:

with hydrogenchloride;sodium hydroxide;nitrogen in diethyl ether;water;

Steps:

5 STAGE C: 2,4-DIHYDROXY-5,6-DIMETHYLBENZALDEHYDE (A. ROBERTSON, W. B. WHALLEY, J. CHEM. SOC., 1949, 3033)

STAGE C: 2,4-DIHYDROXY-5,6-DIMETHYLBENZALDEHYDE (A. ROBERTSON, W. B. WHALLEY, J. CHEM. SOC., 1949, 3033) 4.450 g (32 mmol) of 2,3-dimethyl-5-hydroxyphenol are dissolved in 100 ml of anhydrous ethyl ether in a round-bottomed flask equipped with a gas inlet, a thermometer and a condenser (the outflow gases being trapped by 3 successive bubblers: H₂ SO₄, saturated KMnO₄ solution, 3N NaOH). After 5.635 g (48 mmol) of zinc cyanide have been added, a stream of gaseous hydrochloric acid is passed through for 2 hours with stirring at room temperature. A copious precipitate appears, increasing with the passage of time. At the end of the operation, a powerful stream of nitrogen is passed through the reaction medium. The insoluble matter is separated by filtration and dissolved in boiling water. After cooling, the aldehyde precipitates. After filtration, the crystals are washed with water and dried. Yield: 71% Melting point: 196° C.

References:

US4975455,1990,A