Toluene → 5-(Benzyloxy)pentanoic acid

Temperature

125 °C

δ-Valerolactone (50 g) and toluene (500 mL) were mixed. To the mixture were added potassium hydroxide (158 g) and benzyl bromide (178 mL). The mixture was stirred at 125° C. overnight. To the reaction mixture was added water (350 mL) at ice temperature. The organic layer was removed, and the aqueous layer was washed with tert-butyl methyl ether (150 mL×3). To the resulting aqueous layer were added concentrated hydrochloric acid (75 mL) and 6 N hydrochloric acid (40 mL) at ice temperature. The mixture was extracted with ethyl acetate (250 mL, 100 mL). The combined organic layer was washed with brine (100 mL), then dried over magnesium sulfate. The magnesium sulfate was filtered off and the filtrate was concentrated in vacuo to give the title compound (79.2 g) as a crude product.

1. customThe organic layer was removed
2. washthe aqueous layer was washed with tert-butyl methyl ether (150 mL×3)
3. additionTo the resulting aqueous layer were added concentrated hydrochloric acid (75 mL) and 6 N hydrochloric acid (40 mL) at ice temperature
4. extractionThe mixture was extracted with ethyl acetate (250 mL, 100 mL)
5. washThe combined organic layer was washed with brine (100 mL)
6. dry with materialdried over magnesium sulfate
7. filtrationThe magnesium sulfate was filtered off
8. concentrationthe filtrate was concentrated in vacuo

ORD record

ord-223b385f0b94488fa0d4f944cd38742d

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08604069B2