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How to synthesize aspirin without using acetic anhydride?
Diaspirin [bis(2-carboxyphenyl) succinate; PN508]and fumaryl diaspirin [bis(2-carboxyphenyl) fumarate; PN517] wereprepared as previously described (). Aspirin is commercially available asacetylsalicylic acid, and the synthesis of the other compounds isas described in supplementary information (provided upon request).The compounds tested are shown in .
Isopropyl salicylate was reacted with a slightexcess of 3-bromobenzoyl chloride in the presence of pyridine withno additional solvent. Isopropyl salicylate is availablecommercially but we also prepared small quantities from 2-propanoland salicylic acid by refluxing them with a catalytic quantity ofconcentrated HSO. A ratio of 25 g salicylicacid to 100 ml 2-propanol was used with 1–2 ml of concentratedHSO. After a minimum of 12 h refluxing, theexcess 2-propanol was removed by rotary evaporation. The residue ofoily solid was shaken with 10% NaHCO, with more solidbicarbonate added until all the unreacted salicylic acid haddissolved. This mixture was then extracted well with diethyl etherbefore separating the ether layer, drying over anhydrousMgSO and removing the ether by rotary evaporation. Alow yield (3–5 g; 9–15%) of almost pure isopropyl salicylate (tlc)was obtained and used without further purification. 3-Bromobenzoylchloride was obtained as described for the preparation of PN524above. Isopropyl salicylate (1.90 g) was mixed with pyridine (1.6ml) and was then added carefully to 3-bromobenzoyl chloride (2.38g). An immediate reaction produced a near-solid product. Thereaction vessel was protected with a silica gel guard tube and leftat room temperature for 2–3 days to complete the reaction. Water(20 ml) was added to the tube which was stoppered and shakenvigorously. A sticky oil was released which was taken up in diethylether, washed with 10% NaHCO (20 ml) and then water (20ml). The ether layer was dried over anhydrous MgSO androtary evaporated to give a clear, pale yellow oil (3.4 g; 87%). Asolid product was obtained by dissolving the oil in a little warmdiethyl ether and then diluting with boiling hexane or lightpetroleum ether until a cloudy solution was observed. Storing thismixture at −15°C for 2–3 days gave white crystals [mpt 49–51°C, IR(cm): 2979, 1735, 1703, 1606].
How to synthesize aspirin without using acetic anhydride
HCl salicylic acid + acetyl chloride + 2-picolin ---> O-acetylsalicylic acid + 2-picolin hydrogen chlorideVoluminous crystallization of acetylsalicylic acid The synthesis was thought of rather spontaneously, still I will at some point try to find a useful reference in the literature.
PN525 was prepared in an analogous way using4-methylbenzoyl chloride in place of 3-bromobenzoyl chloride. Theproduct is a white solid and was recrystallized from toluene [mpt148–150°C, IR (cm): 1734, 1674, 1605]. The molar massof the product was confirmed as 256 by titration with standardisedsodium hydroxide using the method described previously ().
representing synthesis aspirin acetyl chloride.
Avoid or minimize: sweeteners, salt, chlorinated water, smoking, peanut products, caffeine and all commercial fats and oils except extra virgin olive oil, do not heat any flesh food or eggs above boiling temperature.
Another useful method is to dissolve one third of a teaspoon of sodium ascorbate in 2 tablespoons of water and from time to time place 20 drops in each nostril.
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Synthesis of aspirin without acetic anhydride? | Yahoo …
The clear, yellow solution which is thereby obtained, is if required, allowed to cool off and is then carefully drop for drop mixed with 1.0 ml (d=1.104; MW=78.50 g/mol; about 1.1 g; 14.0 mmol) of acetyl chloride (if any acetyl chloride is spilled it is best to wipe it up with ethanol - with water acetyl chloride reacts rather violently), whereby an intense warming occurs (approximately up to 50 - 60°C).
The synthesis of aspirin, acetyl salicylic acid, ..
Before each meal take plenty of either fresh barley grass juice, spirulina or chlorella, and try one tablespoon of freshly ground linseed, as well as 1 tablespoon of fenugreek seeds soaked overnight, also use the soaking water.
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