2-Chloroethanol → HCID 14401457, compound

HRID 1193586Notes

Reaction equation

HRID 1193586 reaction equation
[F:1][C:2]([F:14])([C:10]([O:12][CH3:13])=[O:11])[C:3]([F:9])([F:8])[C:4]([O:6][CH3:7])=[O:5].Cl[CH2:16][CH2:17][OH:18].CS(C)=O.[H-].[Na+]>CCOCC.O>[CH3:7][O:6][C:4]1([C:3]([F:9])([F:8])[C:2]([F:14])([F:1])[C:10]([O:12][CH3:13])=[O:11])[O:18][CH2:17][CH2:16][O:5]1

Participants

7

Reactant 4

HCID 342-ChloroethanolHCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 2737124Dimethyl Tetrafluorosuccinate

Product 1

HCID 14401457HCID 14401457, compoundYield 44.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 43.6 g (0.20 mol) of dimethyl tetrafluorosuccinate, 16.1 g (0.20 mol) of 2-chloroethanol, and 100 mL of DMSO was stirred and maintained at 25°-35° while 9.6 g (0.20 mol) of 50% NaH in mineral oil were added portionwise. The resulting mixture was stirred overnight, and then poured into 500 mL of cold water. Ether (300 mL) was added, and the resulting mixture was shaken. After mixture separated into layers, the ether layer was separated, washed with 100 mL of water, dried over CaSO4, filtered and distilled to give 23.1 g (44%) of 2-methoxy-2-(2-methoxycarbonyltetrafluoroethyl)-1,3-dioxolane, b.p. 72°-72.5° at 13 Pa (0.1 mm). IR (neat) and NMR (CCl4) spectra of the product were consistent with the assigned structure.

Workup

  1. additionwere added portionwise
  2. stirringThe resulting mixture was stirred overnight
  3. stirringthe resulting mixture was shaken
  4. customAfter mixture separated into layers
  5. customthe ether layer was separated
  6. washwashed with 100 mL of water
  7. dry with materialdried over CaSO4
  8. filtrationfiltered
  9. distillationdistilled

Sources & evidence

ORD record
ord-0a1296af96d040a194284b7d96aa55a7
Source dataset
uspto-grants-1989_03
Patent number
US04810806

Reaction notes

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