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ChemicalBook CAS DataBase List Salicylaldehyde
90-02-8

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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