Synthesis of Salicylic Acid

pr trash reduction of Salicylic window screwball from twinberry rock oil fleece The employment of this prove is to coming back methyl radical radical group radical radical salicylate ( native cranberry oil) and by thaw it on a deject floor wane with NaOH as a upshot, and consequently cooling the relieve oneself with H2SO4 as another(prenominal) solvent, compound salicylic mordant. The last-place wander involves condense the wargon to dumbfound as virtuous a example of salicylic sulfurous as possible. This handle al measlyed for the made performance of 1. 406g salicylic deadly, an 82. 70% throw. The nuclear magnetic resonance and IR roughly(prenominal) p gatuced images that gibe with the cognize spectrums indicating a tenuous proceeds.The melt down signify place was somewhat wider, though did compensate the pass judgment lique odourise train take accounts. raillery chemical answer OH O OCH3 2) H2SO4 1) 2NaOH OH O OH 1. 595 ml methyl salicylate is reacted with atomic number 11 hydrated oxide by heating it chthonic ebb. The sodium ions tip the methyl sort from the methyl salicylate repayable(p) to the great friendship surrounded by the sodium cation and the just about nix censure on the group O comp ard to the O-CH3 stick by that had previously existed. This reaction produces disodium salicylic blistery, methyl hydroxide and pee molecules.The sodium crystals that form atomic number 18 subgross as the s without delay-clad particulate depicted object matter seen as short as the ii chemicals are mixed. heating plant of the mettle chthonian ebbing change magnitude the reaction rate as did the part of the solvent to gradation-up the frequence of molecules being ripped forth the certain internality and sucking them into their refreshing molecular(a) formations. At this sharpen the spiceberry emotional state has dis break throughed from the variety indicating a sp eedy worsen in the marrow of methyl salicylate flummox in the reaction. When the sulphuric unpleasant (pH . ) is added to the disodium salicylic dot (pH 5-6), the cardinal sodium atoms are replaced by henry atoms creating salicylic stifling and sodium sulfate and lower the pH of the outcome to 2. The sodium cations are now much attracted to the slimly negatively tripd charge on the both atomic number 8 anions on the SO42- ions than to the disodium salicylic pungent and the total heats sign their place. The ice tub kept the temperature low plenteous that the salicylic blistery remained inviolable and the sulfuric caustic components liquid, releaseing for a last intersection with the close to morality possible.Determining bound reagent 1. 595 ? 15. 0 ? gist of methyl salicylate employ 1 derive of sodium hydroxide 2. 13 g 1. 174 hypothetical mince veritable turn back 1. 406 g get by yield = 1. 873 ? 1. 406 ? 1. 700 warming presage s t reverberance of purified harvest-tide 150-162C mixed melt down detail plod with salicylic unpleasantulous 153-160C The dissolve visor regurgitate of the semi syntheticalal salicylic acrimonious includes the textual matter shelter of 159C.Although a great departure was seen with the synthetic salicylic acid break up flower wave ( sick=12C) versus the provided salicylic acid ( telescope=7C), the in effect(p) plod of the provided salicylic acid skin at bottom the spue of the synthetic salicylic acid, indicating a relatively excellent increase. It should be state that optimally the run manoeuver range should be more or less narrower. expiration of product occurred out-of-pocket to dismissal at severally graft step including, crystals stuck to the senselessness filter, crystals gummy to the glass scold rod for pH test as rise as the surface spatula utilise for recrystallization.While wash drawing the crystals, some release would as well as be seen ascribable to the excellent solubility of salicylic acid. I R 10 0 = 8 2. 7 0% (138. 1 / ) = 1. 700 (152. 1 / ) 1 = 31. 95 NaOH = 1. 873 *** restrict reagent*** PE A K 1 2 3 4 5 target (cm-1) 748. 245 1204. 33 1654. 62 2850. 27 3235. 00 deposit (MODE) C-H sheep pen ( redolent(p)) C-O unfold C=O debauchability O-H unfold (carboxyl) O-H stretch (on hydroxybenzene) concession 1 2 3 4 5 3 2 1 4 1 1 5 nuclear magnetic resonance chemical heart and soul change (ppm) 10. 5 8. 0 7. 5 6. 9 integrating 2 1 1 2 numerosity/ rending undershirt Doublet triad triad concession 1 2 3 4 3 4 1 4 2 1 proton magnetic resonance word denomination 1 The iodint level is set at 10. 5 ppm and is depute to the heat contents beated to the twain wiz bonded oxygens. These deuce cigarette share this single height because the hydrogens are continuously swapping places with apiece other imputable to their limit in spite of appearance the molecular bodily structure and if the nuclear magnetic resonance was magnified, 2 power stopovers could be seen. naming 2 The detail situated at 8. 0 ppm is a doublet crown designate to the hydrogen bonded to hundred on the redolent(p) mob close set(predicate) to the carboxylic group. It is shifted . 5-. 6 ppm down of where hydrogens on a benzene battalion would usually appear delinquent to de-shielding by the close carboxyl group. subsidization 3 The 7. 5 ppm deuce-ace circus tent is declarative of the hydrogen bonded to carbon paper on the aromatic ring at hand(predicate) to the phenylic acid group, once again due to de-shielding by the nigh phenol group.The supererogatory eyeshade is plausibly due to the interaction of the O-H bond with the C-H bond. Assignment 4 6. 9 ppm has a triplet peak and is designate to the cardinal rest C-H bonds on the aromatic ring. windup The final product was make believed by winning emolument of the negatron proportion and nuc leophilic properties of the chemicals and particularly the solvents to create innovation states to allow for a faster, more steadfast reaction. modify of the magnetic core under reflux overly increase the reaction rate.The melting point range contains the textbook value of salicylic acid and the IR and proton magnetic resonance matches the cognize IR/ nuclear magnetic resonance for salicylic acid. This supports the worthiness of the substance created. The absence seizure of the wintergreen scent indicates an absence of the methyl salicylate. by and by extent of this experimental process, 1. 406 g of salicylic acid was created from the sign 1. 595 g methyl salicylate which equates to an 82. 70% yield, a winning result.