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Grignard addition to carbonyls

19 real reactions from the literature, on Grignard reagents, esters, aryl ketones and five-membered lactones. Each scheme shows starting materials, conditions and products, with the yield and reference where the source reports them.

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  1. Grignard addition: 1-tetralone (an aryl ketone) with 1) PhMgBr, CH3CH2OCH2CH3, Δ; 2) aq. HCl gives 1-phenyltetralin-1-ol (the benzylic alcohol).
    Grignard additionOrg. Synth. Coll. Vol. 3, p. 729

  2. Grignard addition: a Grignard reagent with CO2 gives 2,4,6-trimethylbenzoic acid (the addition product).
    Grignard additionOrg. Synth. Coll. Vol. 3, p. 553

  3. Grignard addition: a Grignard reagent with 1) CO2; 2) aq. H2SO4 gives 2-methylbutanoic acid (the addition product).
    Grignard additionOrg. Synth. Coll. Vol. 1, p. 361

  4. Grignard addition: tert-butyl 3-(5-methylfuran-2-yl)propanoate (an ester) with 1) propargylmagnesium bromide (2 equiv), Et2O; 2) NH4Cl / H2O gives 4-[2-(5-methylfuran-2-yl)ethyl]hepta-1,6-diyn-4-ol (the tertiary alcohol).
    Grignard additionChem. Eur. J. 2009, 15, 13318

  5. Grignard addition: N-methoxy-N,2-dimethylpropanamide with 1) allylmagnesium chloride, THF; 2) NH4Cl / H2O gives 2-methylhex-5-en-3-one (the dialkyl ketone).
    Grignard additionOrg. Lett. 2014, 16, 6000

  6. Grignard addition: ethyl acetate (an ester) with 1) PhMgBr (2 equiv), Et2O; 2) NH4Cl / H2O gives 1,1-diphenylethanol (the benzylic alcohol).
    Grignard additionOrg. Synth. 1926, 6, 32

  7. Grignard addition: gamma-butyrolactone (a five-membered lactone) with 1) 2-thienylmagnesium bromide (2 equiv), THF; 2) HCl / H2O gives 1,1-dithiophen-2-ylbutane-1,4-diol (the primary alcohol).
    Grignard additionShandong Huagong 2011, 40, 16

  8. Grignard addition: ethyl benzoate (an ester) with 1) PhMgBr (2 equiv.), CH3CH2OCH2CH3, benzene, Δ; 2) aq. H2SO4 gives triphenylcarbinol (the benzylic alcohol).
    Grignard additionOrg. Synth. Coll. Vol. 3, p. 839

  9. Grignard addition: 9-phenanthrenecarbonitrile with CH3MgI; CH3CH2OCH2CH3; Δ gives the addition product.
    Grignard additionOrg. Synth. Coll. Vol. 3, p. 26

  10. Grignard addition: a Grignard reagent with 1) CO2; 2) 20% HCl gives the addition product.
    Grignard additionOrg. Synth. Coll. Vol. 6, p. 845

  11. Grignard addition: gamma-nonalactone (a five-membered lactone) with 1) CH3MgBr (2 equiv.), ether, Δ; 2) HCl, H2O, benzene gives 2-methyldecane-2,5-diol (the secondary alcohol).
    Grignard additionOrg. Synth. Coll. Vol. 4, p. 601

  12. Grignard addition: an α,β-unsaturated ketone with PhMgBr; 1); Et2O; 2) H+ gives the benzylic alcohol.
    Grignard additionRealOChem worksheet

  13. Grignard addition: a Grignard reagent with CO2; −7 °C gives the addition product.
    Grignard additionOrg. Synth. Coll. Vol. 2, p. 425

  14. Grignard addition: cyclohexanone (a six-membered cyclic ketone) with 1); 2) H+ workup gives the benzylic alcohol.
    Grignard additionRealOChem worksheet

  15. Grignard addition: a Grignard reagent with 1) CO2, 0 °C; 2) H3O+ gives pivalic acid (the addition product).
    Grignard additionOrg. Synth. Coll. Vol. 1, p. 524

  16. Grignard addition: an arene and ethyl acetate (an ester) with CH3CH2OCH2CH3; NH4Cl gives 1,1-diphenylethanol (the benzylic alcohol).
    Grignard additionOrg. Synth. Coll. Vol. 1, p. 226

  17. Grignard addition: an alkylbenzene and benzophenone (an aryl ketone) with CH3CH2OCH2CH3; Δ gives the addition product.
    Grignard additionOrg. Synth. Coll. Vol. 2, p. 606

  18. Grignard addition: an ester with PhMgBr; ether, benzene, Δ gives the benzylic alcohol.
    Grignard additionOrg. Synth. Coll. Vol. 3, p. 237

  19. Grignard addition: a Grignard reagent with 1) PhCN, ether, Δ; 2) CH3OH gives benzophenone imine (the addition product).
    Grignard additionOrg. Synth. Coll. Vol. 5, p. 520