Diethoxymethane → HCID 131722756, compound

HRID 1383882Notes

Reaction equation

HRID 1383882 reaction equation
[Cl:1][CH:2]([CH2:5][Cl:6])[CH2:3][OH:4].[CH2:7]([O:9][CH2:10]OCC)[CH3:8]>O.C1(C)C(S(O)(=O)=O)=CC=CC=1>[CH2:7]([O:9][CH2:10][O:4][CH2:3][CH:2]([CH2:5][Cl:6])[Cl:1])[CH3:8]

Participants

4

Reactant 2

HCID 10024DiethoxymethaneHCID 120182,3-Dichloro-1-propanol

Product 1

HCID 131722756HCID 131722756, compoundYield 91.9%

Reagents, catalysts & solvents 1

HCID 124969952-Methylbenzenesulfonic acid hydrateCatalyst

Procedure

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.

Workup

  1. temperatureat reflux
  2. distillationwhile distilling out
  3. additiona mixture of ethanol and DEM
  4. distillation200ml had distilled
  5. addition250 ml fresh DEM was added
  6. waitThe reaction was shut off overnight
  7. customfor 5 hr
  8. custominternal temperature of 99° C
  9. washBase wash
  10. distillationdistillation

Sources & evidence

ORD record
ord-50c61014210e4234b91331351ce47941
Source dataset
uspto-grants-2001_07
Patent number
US06255535B1

Reaction notes

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