Phenol → HCID 86745288, compound

Participants

Reaction Steps

A mixture of the phenol (1 g, 3.7 mmole) of Example 3F, powdered anhhydrous K2CO3 (0.48 g, 3.7 mmole), 18-crown-6 (0.098 g, 0.37 mmole) and acetonitrile (10 mL) is stirred under nitrogen for 15 minutes. 2-Bromomethylnaphthalene (0.496 g, 4.07 mmole) is added and the mixture is placed in an oil bath heated at 65°-70° C. for 10 hours (TLC, dichloromethane-ethyl acetate 8:2). A 10% excess of K2CO3, crown ether and bromomethylnaphthalene is added and the heating is continued for another 4 hours. The acetonitrile is evaporated and the residue dissolved in water and extracted with ethyl acetate (3×). The extracts are washed with 1N-NaOH and brine, dried (MgSO4) and evaporated to dryness. The crude product (1.49 g, waxy solid) is used as such in the next step.

Provenance & Evidence