e| PUBLISHING FOR ONE WORLD NEW AGE INTERNATIONAL (P) LIMITED, PUBLISHERS (formerly Wiley Eastern Limited) New Delhi + Bangalore + Chennai + Guwahati « Hyderabad Jalandhar « Kolkata + Lucknow + Mumbai + Ranchi Visit us at www.newagepublishers.com Copyright © 2003, New Age International (P) Ltd., Publishers Published by New Age International (P) Ltd., Publishers First Edition : 2003 Reprint : 2006 All rights reserved. ‘No part of this book may be reproduced in any form, by photostat, microfilm, xerography, or any other means, or incorporated into any information retrieval system, electronic or mechanical, without the written permission of the copyright owner. ISBN : 81-224-1491-5 Rs. 250.00 2345678910 C-05-12-544 Printed in India at Nagri Printers, Delhi-110 032. PUBLISHING FOR ONE WORLD NEW AGE INTERNATIONAL (P) LIMITED, PUBLISHERS formerly Wiley Eastern Limited) 4835/24, Ansari Road, Daryaganj, New Delhi - 110002 Visit us at www.newagepublishers.comCondensation Reactions 699 F 9 | HO 0 n+ Gh é CH; =— ¢, C—CH, é CH, GH CH,-C-CH, S™ CH,-C-CH,-C- ~ H 0° gu I -H.0 tl GHCH=CH-C-CH, «2 1CH,-¢—CH,-C-CH, H @ Synthesis of benzalacetone from benzaldehyde z ° In a 100ml conical flask place 10ml of freshly distilled benzaldehyde and 20ml of acetone. Keep the flask in cold water bath and then add dropwise with stirring 2.5ml of 10% sodium hydroxide solution such that the temperature does not rise above 30°C. Afier the addition is complete stir the mixture for 2 hours. Add dilute hydrochloric acid to the reaction mixture until it is just acidic and then transfer it to a 250ml separating funnel. Add 20m! chloroform/ether to the separating funnel and shake thoroughly. Remove the organic layer and repeat the process twice, cach time using 20ml of chloroform/ether. Combine the three organic layers, wash with water and then distill on water bath to remove the solvent. Distill the residual portion under reduced pressure and collect the fraction boiling at 150-155°C/ 25mmHg. Cool the distillate which soon solidifies, collect benzalacetone, mp 42°C. (é Synthesis of dibenzalacetone from benzaldehyde ? r 2c4H,cHo + cH,-c-cH, S84, encH-cH-C-CH-cH-cH, In a 100m! conical flask dissolve Sgm of sodium hydroxide in 30ml of water and add 25 ml of 95% ethyl alcohol to it. Cork the flask and then shake it thoroughly taking care that the temperature does not rise above 25°C. Remove the cork add 4ml of acetone and 11ml of benzaldehyde. The colour of the solution immediately changes from yellow to orange. Cork the flask and shake it thoroughly for 30-4Sminutes. Cool the flask and collect the precipitated product by suction filtration on buchner funnel. Wash the product with water so as to remove all the traces of sodium hydroxide, Recrystallise from ethanol and collect yellow crystals of dibenzalacetone, mp 110-112°C.