Benzyl Bromide → Benzyl 5-hydroxypentanoate

Temperature

65 °C

A solution of δ-valerolactone (10 g, 100 mmol) in 1M aqueous sodium hydroxide (100 mL) was heated overnight with stirring at 65° C. The solution was concentrated in vacuo to dryness and any residual water removed under high vacuum at −190° C. The resulting white powder was broken up and suspended in acetone (40 mL). With stirring, benzyl bromide (17 g, 101.4 mmol) and tetrabutylammonium bromide (0.82 g, 2.539 mmol) were added. The mixture was heated at 45° C. with stirring for 72 hours, cooled, and concentrated. The resulting white oily powder was dissolved in ethyl acetate (300 mL) and washed twice each with saturated NaHCO3 and brine. The organic portion was dried over anhydrous MgSO4, filtered, and then concentrated. The result was a yellow oil, which was purified by column chromatography (column 10″L×2″W; eluted with a gradient of 100% hexanes→+30%→50% ethyl acetate in hexanes) to afford the product as a pale yellow oil (3.11 g, 15%).

1. concentrationThe solution was concentrated in vacuo to dryness
2. customany residual water removed under high vacuum at −190° C
3. stirringWith stirring
4. temperatureThe mixture was heated at 45° C.
5. stirringwith stirring for 72 hours
6. temperaturecooled
7. concentrationconcentrated
8. dissolutionThe resulting white oily powder was dissolved in ethyl acetate (300 mL)
9. washwashed twice each with saturated NaHCO3 and brine
10. dry with materialThe organic portion was dried over anhydrous MgSO4
11. filtrationfiltered
12. concentrationconcentrated
13. customwas purified by column chromatography (column 10″L×
14. washeluted with a gradient of 100% hexanes→+30%→50% ethyl acetate in hexanes)

ORD record

ord-0320b1b5615d4a60ba8b690f5d4a5984

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08865675B2