Reacción #62674

ord-5e7e6a073a6747c0a45822ef0a795ac2

Ecuación de reacción

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

Reactantes

O=S(=O)([O-])[O-].[Na+].[Na+]
Na2SO4
—
4-(hydroxyalkyl)thiophenols
—
4-(hydroxyalkyl)phenol
O=S(=O)([O-])[O-].[Na+].[Na+]
Na2SO4
—
4-(hydroxyalkyl)thiophenol
OCCc1ccc(O)cc1
4-(2-hydroxyethyl)phenol
—
4-(hydroxyalkyl)phenols
O=C(O)C(=O)O
oxalic acid
C1=COCCC1
dihydropyran

Reactivos

Ninguno

Disolventes

CC(C)=O
acetone
CC(C)=O
acetone

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.DISTILLATIONdistilled dihydropyran

Procedimiento

Alternatively, suitable 4-(hydroxyalkyl)phenols or 4-(hydroxyalkyl)thiophenols may be protected in one step by combining a solution of the selected 4-(hydroxyalkyl)phenol or 4-(hydroxyalkyl)thiophenol in acetone with Na2SO4, dihydropyran, and a catalytic amount of oxalic acid. For example, 4-(2-hydroxyethyl)phenol in acetone is reacted with Na2SO4, distilled dihydropyran, and a catalytic amount of oxalic acid for three hours to yield 4-(2-tetrahydropyran-2-yloxyethyl)phenol (9).

Fuente

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