Reacción #67491

ord-5ff95af0f63e4a8ea35a299468d96f9b

Ecuación de reacción

[K+].[OH-]
KOH
COc1ccc(C=O)cc1
Anisaldehyde
COC(OC)OC
trimethylorthoformate
Cl
HCl
COc1ccc(C(OC)OC)cc1
title compound
Rendimiento 95.2%
COc1ccc(C(OC)OC)cc1
1-(dimethoxymethyl)-4-methoxybenzene
Rendimiento 95.2%

Reactivos

Ninguno

Disolventes

Condiciones de reacción

Temperatura
12.5°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Temperaturawas warmed to 20-25° C.
  2. 2
    workup.STIRRINGfurther stirred for 10 minutes
  3. 3
    ExtracciónThe reaction mixture was extracted with hexane (2×200 ml)
  4. 4
    Lavadothe combined organic layer was washed with DM water (200 ml)
  5. 5
    ConcentraciónThe organic layer was concentrated below 40° C.

Procedimiento

Anisaldehyde (40 g) and trimethylorthoformate (48.25 ml) were added to MeOH (60 ml) at 20-25° C. and the mixture was cooled to 10-15° C. Conc. HCl (0.26 ml) was then added to the mixture at 10-15° C. and was warmed to 20-25° C. followed by stirring at the same temperature for 16-18 hours. 5% aqueous KOH (40 ml) was added to the reaction mixture at 20-25° C. in 10 min and further stirred for 10 minutes. The reaction mixture was extracted with hexane (2×200 ml) and the combined organic layer was washed with DM water (200 ml). The organic layer was concentrated below 40° C. to obtain title compound (51.0 g, 95.2%).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08524893B2uspto-grants-2013_09