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2,109,833 ‘ Patented Mar. 1, 1938 UNITED STATES PATENT‘ ‘QF‘FICE 2,109,833 NEW COMPOUNDS OF THE BENZOFLUOR ANTHENE‘ SERIES m . ‘ ’ v Werner-.~Zerweck.-and.,Karl Schiitz, Frankfort-on _the¥Main=Fechenh‘eim, Germany, assignorsto . - vGnmeral “Aniline Works, Inc., New York, N. 'Y., ' *acorporationof Delaware 1N0 ,Drawing. ‘Application June 24, 1936, Serial No. 87,012. -.In.»Germany June 29, 1935 (Cl. 260-168‘) v 3 Claims. Our present invention relates to new com that our invention is not'limited to the particu pounds of the benzo?uoranthene series, more_ lar products nor reaction conditions mentioned therein. particularly to those'of the general formula: Example 1 ' X 21.6 parts of 9-(oechlorobenzal) —?uorene of 70°. ' melting point, obtained by condensing ?uorene , ‘X with o-chlorobenzaldehyde, are mixed with 108 parts of caustic potash and about 140 parts of quinoline and the mixture is heated to boiling 10 110’ for about 2 to 3 hours in an apparatus provided With a re?ux condenser andva stirrer. Then the mass'is poured on ice and hydrochloric acid, the precipitate formed .is ?ltered off and recrystal .15 wherein one ‘pair-of PX’s on adjoining carbon atoms standsiiforlalmember selected from the group consisting of two hydrogen atoms and a radiole of the formula: —-CH=CH—CH=CH——, lized if necessary with addition of animal char 15 coal from glacial acetic acid or benzine. The new compound of the formula: and the other pair of X’s stands for two hydrogen 20 20 atoms. The new compounds are obtained by splitting o?” hydrogen halide from a compound of the general formula: 25 X \C/ X Hal forms colorless needles of 167° melting point. Instead of the quinoline there may be employed other high-boiling bases such as for example di 30 30 methylaniline, dimethyltoluidine etc. The same new product is obtained by start ing from 9-(o-chlorobenzyl) -f1uorene of 77° wherein the X’s have the above said signi?cation, or by splitting off hydrogen halide and two hy drogen atoms from a compound of the general formula: melting point, prepared by condensing ?uorene with o-chloro-benzyl-alcohol. Example 2 By treating 9-(o-ch1orobenzal)-2.3-benzo?uo rene (which is prepared by condensing 2.3-benzo ?uorene with o-chlorobenzaldehyde) as described 40 in Example 1, a new hydrocarbon compound of 40 the general formula: Hal 45 45 wherein the X’s have the above said signi?cation. The new compounds may be used as intermedi ates for the production of dyestuffs. In order to further illustrate our invention the following examples are given, the parts being by weight and all temperatures in degrees centi 55 grade. However, we wish it to be understood 50 is obtained, which crystallizes in colorless needles of 230-231” melting point. 55 2,109,833 We claim: 1. Compounds of the benzo?uoranthene series of the general formula: X 2. The 3.4-benzo?uoranthene of the formula: X 10 which crystallizes in colorless needles of 167° melting point and may be used as intermediates for the production of dyestuffs. 15 wherein one 3. A dibenzo?uoranthene obtainable by treat ing 9-(o-chlorobenzal)-2.3-benzo?uorene of the formula: 20 is a, member of the class of 25 / / \/ W H 01 H _. 20 25 and the other \ ——X \C——H 30 H is ll 0-): / C—H / which new benzofluoranthene compounds may be used as intermediates for the production of dye 35 stuffs. with agents suitable for splitting o?f hydrogen halide, which dibenzo?uoranthene crystallizes in 30 colorless needles of 230—231° C. melting point and may be used as intermediate for the produc tion of new dyestuifs. WERNER ZERWECK. KARL SCHUTZ.