Chemistry of hydrocarbon compounds – Aromatic compound synthesis – From nonhydrocarbon feed
Patent
1986-10-20
1987-05-12
Davis, Curtis R.
Chemistry of hydrocarbon compounds
Aromatic compound synthesis
From nonhydrocarbon feed
585 25, C07C 120
Patent
active
046652574
ABSTRACT:
A high yield, four step synthesis process is disclosed for producing the omer, 2,3-diphenyl-1,3-butadiene, wherein in step 1 acetophenone pinacol is produced from the dimerization of acetophenone in 96% yield; in step 2 acetophenone pinacol is reacted with triethoxymethane and benzoic acid to produce 2,3-diphenyl-2-butene in about 88-96% yield. The 2,3-diphenyl-2-butene and N-bromosuccinimide (NBS) are reacted together in step 3 in an ultra violet reactor and in a CCl.sub.4 reaction solvent to produce in about 92% yield, the dibromo compound, 1,4-dibromo-2,3-diphenyl-2-butene. In step 4, 1,4-dibromo-2,3-diphenyl-2-butene is converted to the desired monomer in about 86% yield by reacting with NaI under refluxing conditions for about 90 minutes in a hot acetone solution. The monomer 2,3-diphenyl-1,3-butadiene is recovered in hexane, shaken (in the order listed) with water solutions of NaHSO.sub.3, NaHCO.sub.3, and pure water, dried over CaCl.sub.2, and the hexane is spun off. The residue is then recrystallized from hot methyl alcohol by the addition of water. The crystals which are air dried should be refrigerated as soon as possible to prevent spontaneous polymerization.
REFERENCES:
patent: 3890278 (1975-06-01), Lehn et al.
patent: 4335055 (1982-06-01), Blaser et al.
Organic Syntheses, vol. 50, p. 62, "2,3-Diphenyl-1,3-Butadiene".
Canadian Journal of Research, vol. 17, Sec. B., pp. 80-82.
Bush Freddie M.
Davis Curtis R.
Garvin, Jr. John C.
The United States of America as represented by the Secretary of
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