Reacción #1447075

ord-72893855cf02412e86ff2586278c3a6e

Ecuación de reacción

Cl
HCl
O=C1CCCCCO1
Caprolactone
[K+].[OH-]
potassium hydroxide
CO
methanol
O=C(O)CCCCCO
6-hydroxyhexanoic acid

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Extracciónextracted with ethyl acetate
  2. 2
    LavadoThe combined organic layers were washed with water
  3. 3
    Otrodried
  4. 4
    Filtraciónfiltered
  5. 5
    Concentraciónconcentrated

Procedimiento

Caprolactone (100 g) was added to a mixture of potassium hydroxide (145 g), methanol (110 mL), and THF (390 mL). The resulting mixture was stirred at room temperature overnight. The solution was then acidified with HCl and extracted with ethyl acetate. The combined organic layers were washed with water, dried, filtered, and concentrated to obtain 6-hydroxyhexanoic acid. 1H NMR (CDCl3, 500 MHz) δ 1.44 (m, 2H), 1.60 (m, 2H), 1.68 (m, 2H), 2.37 (t, J=7.5 Hz, 2H), 3.66 (t, J=6.5 Hz, 2H), 5.80 (br, 1H).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07879256B2uspto-grants-2011_02