2-Chloroethanol → HCID 14401463, compound

HRID 345619Notes

Reaction equation

HRID 345619 reaction equation
[CH3:1][O:2][C:3]([F:18])([F:17])[C:4]([C:7]([C:9]([F:16])([F:15])[C:10]([F:14])([F:13])[O:11][CH3:12])=[O:8])([F:6])[F:5].Cl[CH2:20][CH2:21][OH:22].C([O-])([O-])=O.[K+].[K+]>CCOCC>[CH3:12][O:11][C:10]([F:13])([F:14])[C:9]([F:15])([F:16])[C:7]1([C:4]([F:6])([F:5])[C:3]([F:17])([F:18])[O:2][CH3:1])[O:22][CH2:21][CH2:20][O:8]1

Participants

5

Reactant 3

HCID 342-ChloroethanolHCID 11430Potassium CarbonateHCID 1648321,5-bis(Methoxy)perfluoro-3-pentanone

Product 1

HCID 14401463HCID 14401463, compoundYield 60.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 58 g (about 0.2 mol) of crude bis(2-methoxytetrafluoroethyl) ketone, 16.9 g (0.21 mol) of 2-chloroethanol, and 50 mL of ether was stirred while 29.0 g (0.21 mol) of anhydrous K2CO3 were added in portions with cooling. The resulting reaction mixture was stirred overnight, filtered and distilled to give 40.7 g of 2,2-bis(2-methoxytetra- fluoroethyl)-1,3-dioxolane, b.p. 81° at 40 Pa (0.3 mm), m.p. 39°-40° . Dissolution of the resulting filter cake in water, filtration of the resulting mixture and drying gave another 8.5 g of product, m.p. 38.5°-40° , for a total yield of 49.2 g (74%). IR (CCl4) and NMR (CCl4) of the product were consistent with the assigned structure. Anal.: Calcd. for C9H10F8O4 : C, 32.35; H, 3.02; F, 45.48. Found: C, 32.14; H, 3.19; F, 45.22.

Workup

  1. additionwere added in portions
  2. temperaturewith cooling
  3. customThe resulting reaction mixture
  4. filtrationfiltered
  5. distillationdistilled

Sources & evidence

ORD record
ord-c146690df0e44ca296181360185b8fe9
Source dataset
uspto-grants-1991_10
Patent number
US05057586

Reaction notes

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