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ChemicalBook CAS DataBase List Salicylaldehyde

Salicylaldehyde synthesis

14synthesis methods
Salicylaldehyde is synthesized from phenol, chloroform, and alkali according to the Reimer–Tiemman method, which was developed in 1876. starting material for the manufacture of coumarin.
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Yield:90-02-8 100%

Reaction Conditions:

with caesium carbonate in toluene at 80; for 15 h;Sealed tube;Reagent/catalyst;Solvent;Temperature;

Steps:

General procedure for deprotection of triflates

General procedure: Toa solution of aryl triflate 1a-k (0.3 mmol) in distilledtoluene (5 mL) was added Cs2CO3(3 eq.). The suspension was heated at 80 °C (oilbath temp) during 15h. The crude mixture was quenched withethyl acetate (~5 mL) and a saturatedaqueous solution of ammonium chloride (~10 mL).The aqueous layer was extracted with ethyl acetate (2x10 mL). Organic layerswere then combined, dried over MgSO4 and concentratedunder reduced pressure to afford the corresponding phenol 2a-k that was purified byflash chromatography over silica gel.

References:

Green, Alice E.;Agouridas, Vangelis;Deniau, Eric [Tetrahedron Letters,2013,vol. 54,# 51,p. 7078 - 7079] Location in patent:supporting information

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