Organic Syntheses | Page 4

necessary to follow the directions carefully, and what will happen if these directions are not followed.
Although the main object in this series is to give the most convenient laboratory methods for preparing various substances in one-half to five pound lots, an attempt has also been made to have these processes as far as possible adaptable to large scale development. For example, extractions have been avoided wherever possible, cheap solvents have been sub-stituted for expensive ones, and mechanical agitation, a procedure extremely important in the success of many commercial processes, has usually been specified. The apparatus used is always carefully described and wherever necessary an illustration is given. Accompanying each preparation there will be found a bibliography containing references to all the methods for the production of the substance described in the literature. This is given in order to aid any future investigator who may wish to study or improve the methods of preparation. It is not claimed that the methods are, in every case, completely perfect, but only that the yields are very satisfactory and allow the production of the substances at a reasonable cost. It is hoped therefore that the pamphlets will benefit not only the scientific research man of the university, but also the technical chemist who desires to develop the preparation of one of these substances to a large scale process of manufacture. The editors trust also that this work may be used to advantage as a preparation manual in intermediate or advanced courses in organic chemistry in university laboratories, and that it will aid small colleges in the production of necessary reagents which they are often financially unable to purchase.
The pamphlets are to be edited by the following committee: Roger Adams, University of Illinois, Urbana, Illinois; J. B. Conant, Harvard University, Cambridge, Massachusetts; H. T. Clarke, Eastman Kodak Company, Rochester, New York; Oliver Kamm, Parke, Davis Company, Detroit, Michigan; each to act for one year as editor-in-chief and the other three to assist him as associate editors. A new number of the series will appear annually, and every five years the data will be rearranged, revised, corrected, and then published in book form. The number of preparations to be completed yearly is not fixed. There will be, it is certain, about twenty; and it is hoped, as the interest is stimulated in this work, that this number may increase considerably. The editors especially desire to solicit contributions from other chemists, not only in this country but abroad. Whenever a compound is thoroughly and extensively studied in connection with some research, it is hoped that complete directions for its preparation will be assembled and sent to the editor. He will then have them checked and published in a subsequent number. Directions for the preparation of substances already on the market are needed to make this work complete and will be gladly accepted.
It will, of course, be recognized that an occasional mistake or omission will inevitably be found in such a pamphlet as this which contains so many references and formulae. The committee on publication will therefore deem it a favor if they are notified when any such error is discovered. It is hoped also that if any chemist knows a better method for the preparation of any of the compounds considered, or if anyone discovers any improvements in the methods, he will furnish the authors with such information. Any points which may arise in regard to the various preparations will be gladly discussed. In conclusion, the editors are ready to do all they can to make this. work successful, and welcome suggestions of any kind. They feel that the success of the series will undoubtedly depend upon the cooperation of others, and as its success promises to be important to research chemists, the editors urge all interested to assist. THE EDITORS

TABLE OF CONTENTS PAGE I. BENZALACETOPHENONE...........................1 II. BENZYL BENZOATE.............................5 III. BENZYL CYANIDE.............................9 IV. a, g-DICHLOROACETONE..............13 V. _p_-DIMETHYLAMINOBENZALDEHYDE..................17 VI. ETHYL OXALATE...............................23 VII. ETHYL PHENYLACETATE........................27 VIII. GLYCEROL a, g-DICHLOROHYDRIN....29 IX. GLYCEROL a-MONOCHLORORYDRIN............33 X. HYDRAZINE SULFATE............................37 XI. MESITYLENE..................................41 XII. METHYL RED.................................47 XIII. _p_-NITROBENZOIC ACID.......................53 XIV. _p_-NITROBENZYL CYAI~DE......................57 XV. _p_-NITROPHENYLACETIC ACID....................59 XVI. NITROSO-b-NAPHTHOL....................61 XVII. PHENYLACETIC ACID.........................63 XVIII. PHENYLACETYLENE..........................67 XIX. PHENYLHYDRAZINE............................71 XX. PHTHALIMIDE.................................75 XXI. QUINOLINE..................................79 XXII. QUINONE...................................85 XXIII. SODIUM _p_-TOLUENESULFINATE................89 XXIV. 1,3,5-TRINTROBENZENE......................93 XXV. 2,4,6-TRINTROBENZOIC ACID..................95 INDEX.....................................99

ORGANIC SYNTHESES
I
BENZALACETOPHENONE
C6H5CHO + C6H5COCH3 + (NaOH)--> C6H5CH=CHCOC6H5 + H2O
Prepared by E. P. KOHLER and E. M. CHADWELL. Checked by H. T. CLARKE and R. P. LEAVITT.
1. Procedure
A SOLUTION of 218 g. of sodium hydroxide in 1960 g. of water and 1000 g. of 95 per cent alcohol are introduced into a 5500-cc. bottle which is loosely covered with a perforated disk of cardboard, supplied with an effective stirrer, and supported in a larger vessel so as to permit cooling with cracked ice. Into the alkaline solution, 520 g. of pure acetophenone is poured, the bottle is rapidly