Acyloin Condensation

L. Bouveault, R. Loquin, Compt. Rend. 140, 1593 (1905).

Reductive coupling of esters by sodium to yield acyloins (α-hydroxyketones). Yields are greatly improved in the presence of trimethylchlorosilane:

K. T. Finley, Chem. Rev. 64, 573 (1964); K. Ziegler, Houben-Weyl 4/2, 729-822 (1955); S. M. McElvain, Org. React. 4, 256 (1948); J. J. Bloomfield et al., ibid. 23, 259 (1976); R. Brettle, Comp. Org. Syn. 3, 613-632 (1991). Cf. Benzoin Condensation.