Modification of the Grignard reaction - Journal of Chemical Education

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A Modification of the Grignard Reaction As a ~ ~ n s e m e n of c eits

nnemt.innsl ~imnlicitvand its broad aonlicabilitv in carbon-carbon bond formation. the Grienard

to make additions of other reagents in this same solvent. Recently a commercial firm2 has reminded us in an advertisement that dichloromethane has high solvent power for magnesium halide etherates end is an excellent solvent for Grignard reactions.:' However, it was not specified whether this solvent bad general utility. We have studied the use of bath dichloromethane and 1,2-diehlaroethane as co-solvents in typical Grignard additions to carbonyl derivatives and find that either mav be used advantaeeauslv. Addition of the carhanvl eomoound as a dichloromethane solution to preformed Grianard

'Kharasch, M. S., and Reinmuth, O., "Grignard Reactions of Nonmetallic Substances," Prentice-Hall, Englewood Cliffs, New Jersey, 1964. %AldrichChemical Co., Inc. Milwaukee, Wis., back cover of June 15,1973 issue of The Journal of Organic Chemistry, for example. D. J. Nelson :'Viehe, H. G., and Reinstein, M., Chem. Ber., 95,2557 (1962). R. DiFraneeseo D. P e t t e r s Indiana University of Pennsylvania Indiana, Pennsylvania 15701

648 1 Journal of Chemical Education