Phenol → 4-(5-Phenoxypentyl)benzyl alcohol

Participants

Reaction Conditions

Reaction Steps

5-Phenoxypent-1-yne--The process described by the Swiss patent [Chem. Abstr. 93: 167896d) was used. Thus, a mixture of 2.8 g sodium hydride, 5.51 g phenol in 40 mL dry tetrahydrofuran (THF) was stirred at 0° C. under argon until hydrogen evolution ceased. To the resultant solution was added 10 mL dry hexamethylphosphoric triamide (HMPA) followed by a solution containing 5-chloropent-1-yne (4.85 g) in 5 mL THF. The solution was heated at 80° C. for 3 days. The cooled (ambient temperature) mixture was diluted with n-hexane and water. The hexane layer was washed with 2×50 mL portions of water, 1×10 mL 10% potassium carbonate and dried (MgSO4). The evaporated extract was distilled (bp 115°-118° C., 23 mm) to give the title compound (69%) as a colorless oil.

Provenance & Evidence