Home >
Community >
Is there any method to synthesize salicylaldehyde from salicylic acid?
Upvote
20
Downvote
+ Chemistry
+ Synthesis
Posted by
OMONJIATE ELIAB PATRICK
Is there any method to synthesize salicylaldehyde from salicylic acid?
Salicylic acid can be converted to salicylaldehyde using a triangular or square wave alternating voltage. The process of this conversion is explained in this paper$\ce{^{1}}$but it is behind paywall so here's the abstract:
The effect of superimposing sinusoidal, triangular, and square‐wave
alternating voltage (aV) on the potentiostatic reduction of salicylic
acid to salicylaldehyde has been studied. Polarization curves with aV
modulation were measured with an amalgamated copper rotating disk
electrode. Enhanced dc current densities were observed with increasing
magnitude of superimposed aV. However, aV frequency and type did not
have significant effect on the resulting dc current densities. Batch
cell electrolysis experiments were conducted with a H‐type cell. The
conversion of salicylic acid and yield of salicylaldehyde were
measured as functions of electrolysis time, aV magnitude, type, and
frequency. The superimposed aV significantly enhanced the reaction
rate, conversion of salicylic acid, and the yield of salicylaldehyde.
The energy consumption of ac electrolysis was higher than that of dc
electrolysis.
doi: 10.1149/1.2100342 J. Electrochem. Soc. 1987 volume 134,issue 12, 3074-3077
Salicylic acid can be converted to salicylaldehyde using a triangular or square wave alternating voltage. The process of this conversion is explained in this paper$\ce{^{1}}$but it is behind paywall so here's the abstract:
The effect of superimposing sinusoidal, triangular, and square‐wave alternating voltage (aV) on the potentiostatic reduction of salicylic acid to salicylaldehyde has been studied. Polarization curves with aV modulation were measured with an amalgamated copper rotating disk electrode. Enhanced dc current densities were observed with increasing magnitude of superimposed aV. However, aV frequency and type did not have significant effect on the resulting dc current densities. Batch cell electrolysis experiments were conducted with a H‐type cell. The conversion of salicylic acid and yield of salicylaldehyde were measured as functions of electrolysis time, aV magnitude, type, and frequency. The superimposed aV significantly enhanced the reaction rate, conversion of salicylic acid, and the yield of salicylaldehyde. The energy consumption of ac electrolysis was higher than that of dc electrolysis.
doi: 10.1149/1.2100342 J. Electrochem. Soc. 1987 volume 134,issue 12, 3074-3077
I suspect that reduction of salicyclic acid with LAH can afford o-cresol. Salicyl alcohol, as its oxygen bound aluminate salts, can eliminate to form 2-methylene cyclohexadienone, which suffers reduction to o-cresol. Compare mixed anhydride reduction of salicylic acid with NaBH4. Synthesis, 2479 (2005). A fair comparison is the LAH reduction of indole-3-carboxaldehyde to 3-methylindole (skatole).More
Salicylic acid can be converted to salicylaldehyde using a triangular or square wave alternating voltage. The process of this conversion is explained in this paper$\ce{^{1}}$but it is behind paywall so here's the abstract:
Salicylic acid can be converted to salicylaldehyde using a triangular or square wave alternating voltage. The process of this conversion is explained in this paper$\ce{^{1}}$but it is behind paywall so here's the abstract:
More
VOTE
It's simple. Reduce with LAH then oxidise it with PCC or PDC.
It's simple. Reduce with LAH then oxidise it with PCC or PDC.
More
VOTE
VOTE
VOTE
VOTE