Decarbalkoxylation of carboxylic acid esters

Details Decarbalkoxylation of carboxylic acid esters Decarbalkoxylation of carboxylic acid esters

1977-08-08

1981-06-30

Trousof, Natalie

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

560 1, 560 9, 560 18, 560103, 560105, 560122, 560123, 560124, 560128, 560152, 560174, 560205, 560219, 560265, 2604109R, 260464, 260465R, 260465H, 2604651, 2604657, 2604658R, 2604659, 568314, 568346, 569392, C07C 6732, C07C 4565, C07C12000

Patent

active

042762251

ABSTRACT:
A carboxylic acid ester activated in .alpha.-position by a keto, ester or nitrile group, i.e. of the formula ##STR1## where X is COOR.sup.4, COR.sup.5 or CN, and the several R's can have various meanings but only R.sup.1 and R.sup.2 can be hydrogen, is decarbalkoxylated by heating in the presence of a salt, e.g. sodium chloride, and a phosphorus-containing solvent such as a phospholine oxide, phospholane oxide or phosphetane oxide of the formulas ##STR2## wherein a-k and R can have varied definitions. Water is present either at the outset or end of the reaction before product separation. The reaction proceeds smoothly and in good yields.

REFERENCES:
patent: 2663737 (1953-12-01), McCormack
patent: 2663739 (1953-12-01), McCormack
patent: 3816524 (1974-06-01), Grinstead
Krapcho et al., "Decarboxylation of Geminal Diesters . . . ", Tetrahedron Letters (1973) No. 12, pp. 957-960.
Krapcho et al., (above subject continued) Ibid (1974), No. 13, pp. 1091-1094.

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