Hydrochloric Acid → Hexanoic acid, 6-(phenylmethoxy)-

Participants

Reaction Steps

ε-caprolactone (10 mL, 0.18 mol), benzyl bromide (13.4 mL, 0.11 mol), and potassium hydroxide (11.3 g, 0.281 mol) were dissolved in toluene (200 mL). The reaction flask was placed in a 120° C. pre-heated oil bath and refluxed overnight under stirring. The mixture was then neutralized using 1 M HCl (300 mL), the toluene evaporated off, and the product extracted using dichloromethane (3×300 mL) to afford a mixture of mono and di-protected 6-hydroxy-hexanoic acid. The crude product was saponificated with 1M sodium hydroxide (200 mL) and methanol (200 mL), extracted with dichloromethane (3×200 mL), and the solvent was evaporated under reduced pressure to afford pure 6-benzyloxy-hexanoic acid (72% yield). 1H NMR (CDCl3) 1.38-1.46 (m, 2H, CH2), 1.57-1.68 (m, 4H, CH2CH2), 2.32-2.38 (m, 2H, CH2COOH), 3.42-3.46 (m, 2H, OCH2), 4.48-4.53 (s, 2H, PhCH2), 7.27-7.31 (m, 5H, aromatic).

Provenance & Evidence