Diethoxymethane → HCID 131722756, compound

Participants

Reaction Steps

A mixture of 516 g (4.0 mol) 2,3-dichloro-1-propanol, 2.0 g toluenesulfonic acid hydrate, and 1500 ml (12.0 mol) diethoxymethane (DEM) was stirred at reflux while distilling out a mixture of ethanol and DEM. After 5 hr, 200ml had distilled and 250 ml fresh DEM was added. The reaction was shut off overnight and resumed the next day for 5 hr, reaching a final internal temperature of 99° C. Base wash and distillation yielded 688 g of C2H5OCH2OCH2CHClCH2Cl, bp 60-70° C./0.3 mm. Of this amount, 210.7 g was fluorinated in PMM as in Example 1 and the product analyzed by 19F NMR as containing C2F5OCF2OCF2CFClCF2Cl in 69% yield, accompanied by the 1,3-dichloride isomer in about 5% yield. Distillation gave the main cut bp 110° C., 96% pure by glc.

Provenance & Evidence