Reacción #554569

Ecuación de reacción

H2SO4

oxacyclotridecan-2-one

methanol

→

14c

Rendimiento 88.0%

Methyl-12-hydroxy-dodecanoate

Rendimiento 88.0%

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroMethanol was removed under reduced pressure
2. 2
   Extracciónthe aqueous residue was extracted with diethyl ether 3 times
3. 3
   LavadoThe combined organic layers were washed with saturated NaHCO3, saturated NaCl
4. 4
   Secadodried over MgSO4
5. 5
   OtroThe diethyl ether was removed under reduced pressure

Procedimiento

Concentrated H2SO4 (0.2 mL) was added to a solution of oxacyclotridecan-2-one (850 mg, 4.3 mmol) in 20 mL of methanol and stirred for 1 day. Methanol was removed under reduced pressure and the aqueous residue was extracted with diethyl ether 3 times. The combined organic layers were washed with saturated NaHCO3, saturated NaCl, and then dried over MgSO4. The diethyl ether was removed under reduced pressure to yield 874 mg (88%) of 14c as a white solid. 1H-NMR (400 MHz, CDCl3, δH ppm): 3.65 (3H, s, CO2CH3), 3.63 (2H, t, 3JH—H=6.6 Hz, HO—CH2), 2.29 (2H, t, 3JH—H=7.6 Hz, CH2CO2), 1.50-1.66 (4H, m, 2CH2), 1.22-1.38 (14H, m, 7CH2). HRMS (EI): m/z calcd 231.1955 ([M+H]+, C13H27O3), found 231.1954 [M+H]+.

Fuente