Toluene → 1-Pentyn-3-ol, 3-methyl-1-phenyl-

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Reaction Steps

Phenylacetylene (500 g, 4.2 mol) was added to a mixture of potassium hydroxide flake (290 g) and toluene (3 L). 2-Butanone (425 g, 5.9 mol) was added over 45 minutes keeping the temperature below 30° C. with periodic cooling and the resulting mixture agitated for 20 h at room temperature. Water (1 L) was added, the toluene solution washed until neutral, the solvent evaporated, and the residue distilled to give 517 g (71% yield) of 3-methyl-1-phenyl-1-pentyn-3-ol; bp 107°-110° C./3 mm; IR (film) 3400, 1150, 1000, 920 cm-1 ; NMR (CDCl3) 1.1 (3H, t), 1.6 (3H, s), 1.8 (2H, q), 2.2 (1H, s), 7.2-7.6 (5.H, m) δ; MS (m/e) 174, 156, 145, 43.

Provenance & Evidence