Resorcinol dibenzoate

The benzoylation of resorcinol to produce 2,4-dihydroxybenzo-phenone has been previously performed with benzotrichloride, which implies the coproduction of 3 mol of hydrochloric acid and consequently a large amounts of acid waste. " Alternative routes to 2,4-dihydroxyben-zophenone involve direct acylation of resorcinol with benzoyl chloride (BC) or the Hoesch reaction with benzonitrile, which also suffer from acid waste production. In a more ecoefficient approach, the reaction was performed with benzoic acid (BAC) in the presence of some solid catalysts, with a special focus on BEA zeolite (Scheme 5.9). The progress of the reaction in para-chlorotoluene is examined, and after 18 h, 2,4-dihy-droxybenzophenone (2,4-DHB) is isolated in 70% yield, together with 20% of resorcinol monobenzoate (RMB), 3% of resorcinol dibenzoate, 5% of BAC, and 2% of resorcinol. The fact that the concentration of resorcinol in the final mixture is somewhat lower than that of BAC is probably due to the preferred adsorption of the former. The process is then studied by using different substituted BACs the different conversions of 2-methyl-,... 

Raney nickel, 135, 312,411 Ratcliffe reagent, 37, 70 Redudion decyanization, 324-325 Reductive dimerization, 369 Reformatsky-type reactions, 151-152 Resolution, 79,113 Resorcinol dibenzoate, 57 Retinal, 372 Retroaldol reaction, 303 RhodiumGl) acetate, 76, 313 Rhodium(II) n-butanoate, 313 Rhodium(II) carboxylates, 313 Rhodium(III) chloride, 313-314 Rhodium(III) chloride-Triphenylphosphine, 314... 

With para-chlorotoluene as solvent, after 18 h 2,4-dihydroxybenzophenone (26) is isolated in 70% yield, together with 20% of resorcinol monobenzoate (27) and 3% of resorcinol dibenzoate. 

Also obtained by saponification of 2,4-di(benzoyloxy)benzophenone with 10% sodium hydroxide in refluxing ethanol for 2 h [203] or with potassium hydroxide in ethanol [210], The starting diester was prepared by Fries rearrangement of resorcinol dibenzoate with zinc chloride at 100-120° [210],... 

Preparation by Fries rearranganent of 2-nitro-resorcinol dibenzoate with aluminium chloride in nitrobenzene at 100-110° for 3 h (40%) [1207]. 

Preparation by saponification of 4,6-di-(benzoyloxy)-1,3-dibenzoylbenzene (SM) with potassium hydroxide in refluxing ethanol [203,210], The keto ester SM was obtained by acylation of resorcinol dibenzoate with benzoyl chloride in the presence of zinc chloride at 100-120 during several days [210]. 

Also obtained by photo-Fries rearrangement of resorcinol dibenzoate in benzene for 8 h under nitrogen (15%) [843]. 

Obtained by action of benzoyl chloride with resorcinol dibenzoate in the presence of aluminium chloride at 100° for 8 h, then at 150° [145]. 

The dihydrobenzoxathiin 408, a potent selective estrogen receptor alpha modulator, is metabolized to the bridged dibenzo[, 4]thiopyran derivative 409. It seems logical to assume that 409 is formed by initial cleavage of the O-C bond followed by an intramolecular acylation to generate the thiopyran ring. A 19-step total synthesis from resorcinol confirmed the structure of 409 (Equation 115) <20050L411>. 

Translational isomerization of a series of [2]catenanes possessing an electron-rich dibenzo-34-crown-10 ether interlocked with rings containing an unsymmetrical 4-substituted resorcinol-based tether linking two electron-poor dipyridinyl groups was demonstrated and studied by VT NMR <07CC4289, 07JOC6454>. 

As hereinbefore pointed out, the 5-(tertiary alkyl)resorcinols thus prepared in accordance with this invention are important intermediates in the preparation of useful drugs. For example, 5-(l,l-dimethyl-heptyl)resorcinol is utilized in the preparation of l-hydroxy-3-(l,l-dimethylheptyl)-6,6a,7,8,9,l 0,10a-hexahydro-6,6-dimethyl-9H-dibenzo[b,d]pyran-9-one, which compound is extremely useful in the treatment of depression in humans, as described in U.S. Pat. Nos. 3,928,598, 3,944,673, and 3,953,603. Similarly, 5-(l,l-dimethyl-heptyl)resorcinol is required in the synthesis of3-(l,l-dimethylheptyl)-6a,7,8,9,10,10a-hexahydro-6,6-dimethyl-6H-dibenzo[b,d]pyran-l,9-diol, which compound is useful as a blood-pressure lowering agent. It can thus be seen that a commercially feasible process for preparing 5-(tertiary alkyl)resorcinols in high yield is desirable. 

Pyrolysis of tri-, tetra-, and penta-chlorobenzenes affords mixtures of chlorinated dibenzofurans and dibenzo-p-dioxins, " and chlorinated diphenyl ethers cyclize in the presence of palladium acetate to polychloro-dibenzofurans/ The action of malononitrile on tetrahydroxy-p-benzoquinone leads to the benzo-difuran (79), contrary to a previous report/ The acid-catalysed condensation of quinones with phenols has been studied p-benzoquinone and resorcinol, for example, afford compound (80)/ Naphtho[2,3- >]furan-4,9-diones (81 R = Me or Ph R = Ac, Bz, C02Et, or CN) are obtained from 2,3-dichloronaphtho-1,4-quinone and compounds R COCHaR in DMF that contains potassium fluoride/ The action of mineral acids on p-benzoquinone produces a mixture of complex benzofurans, which includes (82) and (83)/ Bases convert the ben-zofuranone (84) into the tetrameric compound (85), contrary to an earlier... 

PEG-75 lanolin PEG-2 stearate PEG-2 tallowate Propylene glycol laurate plasticizer, thermoplastic elastomers Poly-a-methylstyrene plasticizer, thermoplastic polyesters Resorcinol bis (diphenylphosphate) plasticizer, thermoplastic urethane Poly-a-methylstyrene plasticizer, thermoplastics Neopentyl glycol dibenzoate plasticizer, thermoplastics/thermosets Ethyl toluenesulfonamide p-Toluenesulfonamide plasticizer, thermoset polyesters Tris (2,3-dichloropropyl) phosphate plasticizer, tire components Asphalt, oxidized plasticizer, toys Epoxidized soybean oil plasticizer, transfer inks Dibutyl tartrate... 

Phenoxyethanol Resorcinol bis (diphenylphosphate) Triacetin Tributyl phosphate Tridecyl adipate Triethylene glycol Triethylene glycol dibenzoate Trimethylol pentanediol dibenzoate Trioctyl phosphate plasticizer, vulcanizing elastomers Polychloroprene plasticizer, wall-tile mastics PEG hydrogenated castor oil plasticizer, water repellents Dimethiconol... 

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