Reaction #364746

Reaction equation

vinylacetate

OEt2

trimethyl ortho formate

vinylacetate

1,4-benzoquinone

BF3

→

1,1,3-Trimethoxy-3-acetoxypropane

Conditions

Workup

1. 1
   Otherlow boiling impurities were removed from the reaction mixture through the application of a slight vacuum
2. 2
   OtherIn a comparative experiment, without removal of low boiling impurities
3. 3
   OtherBoth reaction mixtures

Procedure

A mixture of 56.00 g trimethyl ortho formate, 60.00 g vinylacetate, 0.75 g PdCl2(ACN)2, 0.60 g 1,4-benzoquinone, and 1.00 ml BF3*OEt2 was stirred at 30° C., and low boiling impurities were removed from the reaction mixture through the application of a slight vacuum. A fractionation column was installed to prevent losses of starting materials and/or products. After 2.3 hours, the ratio of 1,1,3,3-tetramethoxypropane to 1-acetoxy-1,3,3-trimethoxypropane, and the isomeric 1,3-diacetoxy-1,3-dimethoxy-propanes was determined by CG-analysis to be 1.0:2.4:1.3 on the basis of the FID-area-percentages. In a comparative experiment, without removal of low boiling impurities, the referring ratio was determined to be 1.0:1.48:0.50. Both reaction mixtures still contained an excess of vinylacetate.

Source