(i Synthesis of Dimethy! Oxalate from oxalic acid:- COOH CoocH, +2CH,OH —> +2H,0 COOH COocH, Place 10 gm of powdered oxalic acid in a porcelain dish and heat on a wire gauze till no more water is given off. During the heating process the acid should be stirred and powdered. Transfer the anhydrous acid in a 100m! round bottom flask fitted with a reflux condensor. Add 25ml anhydrous methyl alcohol to the flask and reflux the resultant solution on water bath for 3hours. Set the apparatus for downward distillation and distill off the excess methanol on water bath. Distill the residual concentrate on wire gauze and collect the fraction boiling at 160-165°C. Cool this distillate which soon solidifies and then filter it on a Buchner funnel. Recrystallise dimethul avalate fram ethvl alenhal and dru mn S490 f Vield £7 am)NH, NHCOCH, + (CH,CO),0 —> O +CH,COH Ina 100 ml round bottom flask fitted with a reflux condensor place Sm! of aniline and 10 ml of 1:1 acetic acid and acetic anhydride mixture (Sm! acetic acid and 5 ml acetic anhydride). Heat the mixture gently under reflux for 15-20 minutes on oil bath and then pour the contents while still hot with stirring into a 200ml beaker containing 100ml ice cold water. Stir the mixture vigorously to hydrolyse the excess acetic anhydride. After all the acetanilide has precipitated, collect it on buchner funnel and wash with cold water. Recrystallise the crude product from boiling water. If the product is excessively coloured add a pinch of animal charcoal to hot water and filter hot through glass wool/ cotton plug. Pure colourless crystals of acetanilide melts at 114°C (5-5.5g) Note : Acetanilide is medicinally important as it is used as febrifuge (antifibrin) H-N-H H- tle R ess é- CH, a HN-C-—CH, +CH,CO,H