A New Modification of the Ullmann Synthesis of Fluorene Derivatives

Abstract

moved and the residual viscous red oil treated with 5 cc. of boiling petroleum ether (b. p. 60-110"). The insoluble dark gum was removed from the solution by decantation of the latter. On cooling, the petroleum ether deposited an orange-colored solid which weighed 235 mg. By concentrating the mother liquors, carefully discarding the red gum which formed regularly, another 540 mg. of this solid was obtained. The total yield was 775 mg. (26%). A sample was recrystallized from petroleum ether (Darco) to constant melting point; tiny needles, m. p. 146' (cor.). Anal. Calcd. for C~lH2604: C, 72.88; H, 7.89. Found: C, 73.55; H, 7.82.l-Hydroxy-J-n-amyl-9-rnethyl-6-dibenzopyrone.-A mixture of 235 mg. of 2,6-dimethoxy-4-n-amyl-5'-methyl-2'-carboxybiphenyl, 0.6 cc. of 48% hydrobromic acid, 1 cc. of glacial acetic acid, and 0.5 cc. of acetic anhydride was heated to reflux to dissolve the solid acid, and heating continued for four hours. After pouring into 20 cc. of water, the reaction mixture was extracted three times with ether and the organic layer washed thoroughly with saturated aqueous sodium bicarbonate and dried over magnesium sulfate. The solvent was removed and the oily residue was treated with boiling petroleum ether (b. p.

ChemInform Abstract: STEREOSELECTIVE IN‐VITRO AROMATIC‐RING OXYGENATIONS OF CHIRAL 1,4‐BENZODIAZEPIN‐2‐ONES

“…Determined in acetone-ds (except 40 in MeOH-d4). Preparation described in [47], but no data presented there. Described in [441, m.p.…”

Palladium‐Catalyzed Oxidative CH Bond Acylation of Acetanilides with Benzylic Alcohols

“…It was found that 59% 3-(2-acetamido)-naphthyl phenyl ketone [14] was isolated when b-acetylnaphthylamine was reacted with phenylmethanol as substrates (entry 9).…”

Fulvenes and Thermochromic Ethylenes. Part 70 Syntheses in the Dibiphenylene‐Ethene (Bifluorenylidene) Series

“…For the preparation of I-methyl-fluorenone (VII) the treatment of 2-chloro-2'methylbenzophenone with potassium hydroxide in quinoline [13] and the diazotization and "Verkochung" of2-amino-2'-methylbenzophenone [14,15] have been pro-424 (I) I. GOSNAY ET AL.…”