2-Chloroethanol → HCID 14401457, compound

HRID 345618Notes

Reaction equation

HRID 345618 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. Anal.: Calcd for C8H10F4O5 :C, 36.65; H, 3.85; F, 28.99. Found: C, 36.45; H, 3.95; F, 28.70.

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-17efde729a504172899a9c4e4775a4be
Source dataset
uspto-grants-1991_10
Patent number
US05057586

Reaction notes

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