Reacción #62685

ord-1d2b9189a80b40619fd519eb29ed46e4

Ecuación de reacción

O=C(O)C(=O)O
Oxalic acid
O=S(=O)([O-])[O-].[Na+].[Na+]
Na2SO4
C1=COCCC1
dihydropyran
OCCc1ccc(O)cc1
4-(2-hydroxyethyl)phenol
[Na+].[OH-]
NaOH
Oc1ccc(CCOC2CCCCO2)cc1
4-(2-tetrahydropyran-2-yloxyethyl)phenol

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Lavadowashed with CH2Cl2 (2X)
  2. 2
    workup.STIRRINGThe mixture was stirred vigorously for one hour
  3. 3
    LavadoThe organic phase was washed with water (3×1 l)
  4. 4
    Otroevaporated

Procedimiento

Oxalic acid (64 g, 0.5 mol), Na2SO4 (400 g) and distilled dihydropyran (600 mL) are added to a solution of 4-(2-hydroxyethyl)phenol (600 g, 4.3 mol) in acetone (3 l) and the mixture stirred for 3 hours. The resulting solution is added to water (4 l) containing 35% NaOH solution (500 mL), and washed with CH2Cl2 (2X). The mixture was stirred vigorously for one hour. The organic phase was washed with water (3×1 l) and evaporated to yield 4-(2-tetrahydropyran-2-yloxyethyl)phenol (9).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US04761420uspto-grants-1988_08