Cyclohexene oxide → Cyclohexanol, 2-phenoxy-

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Reaction Steps

Cyclohexene oxide (10 g, 0.102 mol) was added dropwise to an aqueous solution of sodium phenoxide trihydrate (31.6 g, 0.186 mol; 250 mL). The mixture was refluxed overnight, cooled to room temperature, and a precipitate was collected by filtration. The precipitate was dissolved in ethyl acetate. The organic phase was washed with 1 M NaOH, brine, dried (over MgSO4), and concentrated to give solid 2-phenoxy-cyclohexanol (a compound of general Formula II) (13.84 g, 70%). The melting point of this compound was determined to be 79-80° C. 1HNMR (CDCl3 ): δ7.3 (m, 2H), 6.9 (m, 3H), 4.0 (m, 1H), 3.7 (m, 1H), 2.1 (m, 2H), 1.8 (m, 4H), 1.4 (m, 4H) ppm.

Provenance & Evidence