ChemicalBook CAS DataBase List 3,5-DICHLORO-4-HYDROXYBENZALDEHYDE

3,5-DICHLORO-4-HYDROXYBENZALDEHYDE synthesis

8synthesis methods

Product Name:3,5-DICHLORO-4-HYDROXYBENZALDEHYDE
CAS Number:2314-36-5
Molecular formula:C7H4Cl2O2
Molecular Weight:191.01

2432-12-4

2314-36-5

General procedure for the synthesis of 3,5-dichloro-4-hydroxybenzaldehyde from 2,6-dichloro-4-methylphenol: A mixture of the substrate 2,6-dichloro-4-methylphenol (1 mmol), cobalt salts (n1 mol%), and NaOH (n2 equiv.) in ethylene glycol (5 mL) was subjected to a stirring reaction under an atmosphere of oxygen (1 atm) at 80°C for 8 hours. Upon completion of the reaction, hydrochloric acid (10 mL, 2%) and methyl tert-butyl ether (MTBE, 10 mL) were sequentially added to the reaction mixture. The organic layer was separated and the aqueous phase was further extracted with MTBE (10 mL x 2). All organic phases were combined, dried with anhydrous sodium sulfate and concentrated to obtain the residue. The residue was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate, 10:1, v/v) to afford the target product 3,5-dichloro-4-hydroxybenzaldehyde.

123-08-0 Synthesis

123-08-0
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2314-36-5
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$12.00/250mg

Yield: 97.4%

Reaction Conditions:

with N-chloro-N-(benzenesulfonyl)benzenesulfonamide in acetonitrile at 20 - 25; for 0.666667 h;Green chemistry;

Steps:

General procedure for the dichlorination reaction
General procedure: To a solution of 4-nitroaniline, 1b (0.99 g, 7.2 mmol) in 7 mL specially dried MeCN was added N-chloro-N-(phenylsulfonyl)benzene sulfonamide (4.8 g, 14.4 mmol) in a 25 mL round bottom flask. The reaction mixture was stirred for 10-15 minutes at 20-25 °C, monitored by GC. After completion of the reaction, MeCN was distilled under vacuum at 40-45 °C. The residue was treated with 20 mL mixture of MDC and water, stirred the mixture for 10-15 minutes; MDC layer was separated and washed with 5 % sodium bicarbonate solution, after separation MDC layer was dried over sodium sulfate and evaporated under vacuum to obtain 2,6-dichloro-4-nitroaniline, 2b produced 1.45 g (99.0 % yield, 99.2 % purity) as a yellow powder.

References:

Misal, Balu;Palav, Amey;Ganwir, Prerna;Chaturbhuj, Ganesh [Tetrahedron Letters,2021,vol. 63,art. no. 152689] Location in patent:supporting information

2432-12-4
103 suppliers
$27.00/1g

2314-36-5
136 suppliers
$12.00/250mg

References

22002-17-1 Synthesis