Water → p-(Pentyloxy)acetophenone

Participants

Reaction Conditions

Reaction Steps

To a solution of the 4-hydroxyacetophenone (1.0 g, 7.3 mmol) in 5 mL DMF under Ar was added K2CO3 (1.0 g, 7.3 mmol) and 1-bromopentane (1.1 mL, 8.7 mmol) and heated at 60° C. overnight. The reaction mixture was cooled to room temperature, poured into water (100 mL) and extracted with EtOAc. The organic layer was washed with brine, dried and evaporated to afford a residue which upon purification by combiflash, eluting with 5% EtOAc in Hexane afforded 1.3 g product (86%). 1H NMR (500 MHz, CDCl3): δ 0.98 (t, 3H, J=7.0 Hz), 1.41-1.49 (m, 4H), 1.83-1.86 (m, 2H), 2.59 (s, 3H), 4.09 (t, 2H, J=6.5 Hz), 6.98 (d, 2H, J=7.0 Hz), 7.98 (d, 2H, J=7.0 Hz).

Provenance & Evidence