Benzyl Alcohol → Benzyl 5-bromopentanoate

Participants

Reaction Conditions

Reaction Steps

To a dry, nitrogen purged 100 mL round bottomed flask was added benzyl alcohol (2.98 g, 0.027 mol), triethylamine (2.79 g, 0.027 mol) and CH2Cl2 (50 mL). The solution was stirred and cooled to 0° C. and 5-bromovaleryl chloride (5.00 g, 0.025 mol) added dropwise. A white suspension formed and this mixture was stirred at 0° C. for 0.5 h then warmed to rt over 1 h. After stirring at rt for 15 h, the suspension was poured into water (100 mL) and the phases separated. The aqueous layer was extracted with CH2Cl2 (1×100 mL) and the combined CH2Cl2 layers were dried over Na2SO4. Filtration and concentration produced a light brown suspension, which was diluted with EtOAc (50 mL) and then re-filtered. After concentration, the resulting amber oil was chromatographed on silica gel using 10% EtOAc in hexanes to give 6.79 g (100%) of Preparation 12 as a clear, colorless oil. Rf=0.80 (SiO2, 50% EtOAc in hexanes). 1H NMR (500 MHz, CDCl3): δ=7.33 (m, 5H), 5.11 (s, 2H), 3.38 (t, J=6.5 Hz, 2H), 2.38 (t, J=7.0 Hz, 2H), 1.88 (m, 2H) and 1.79 (m, 2H).

Provenance & Evidence