Water → 2-Phenoxy-2-trifluoromethyl-1,3-dioxolane

HRID 483890Notes

Reaction equation

HRID 483890 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[F:10][C:11]([F:19])([F:18])[C:12]([O:14][CH2:15][CH2:16]Cl)=[O:13].O>CS(C)=O>[O:7]([C:12]1([C:11]([F:19])([F:18])[F:10])[O:14][CH2:15][CH2:16][O:13]1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 996PhenolHCID 24758Sodium hydrideHCID 125747172-Chloroethyl trifluoroacetate

Product 1

HCID 144014482-Phenoxy-2-trifluoromethyl-1,3-dioxolaneYield 47.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of 23.5 g (0.25 mol) of phenol in 50 mL of DMSO was added dropwise to a stirred suspension of 12.0 g (0.25 mol) of 50% NaH in mineral oil in 100 mL of DMSO maintained at 15°-20° by cooling. After evolution of gas had slowed, cooling and stirring were continued while 44.3 g (0.25 mol) of 2-chloroethyl trifluoroacetate were added. The temperature of the reaction mixture was kept below 30° while the exotherm which occurred subsided, then the resulting mixture was stirred overnight, poured into 1 L of water, and extracted with 200 mL, then two 100 mL portions, of ether. The resulting ether solutions were washed with water, dried over CaSO4, and distilled to give 27.6 g (47% yield) of 2-phenoxy-2-trifluoromethyl-1,3-dioxolane, b.p. 52°-54° at 80 Pa (0.6 mm). IR (neat) and NMR (CCl4) spectra were consistent with the assigned structure. Anal.: Calcd for C10H9F3O3 : C, 51.29; H, 3.87; F, 24.34. Found: C, 51.19; H, 3.92; F, 24.49.

Workup

  1. temperaturemaintained at 15°-20°
  2. temperatureby cooling
  3. temperaturecooling
  4. additionwere added
  5. customwas kept below 30° while the exotherm which
  6. stirringthe resulting mixture was stirred overnight
  7. extractionextracted with 200 mL
  8. washThe resulting ether solutions were washed with water
  9. dry with materialdried over CaSO4
  10. distillationdistilled

Sources & evidence

ORD record
ord-b7ed815ab0894616a0d3ed980f68ddc5
Source dataset
uspto-grants-1993_07
Patent number
US05227500

Reaction notes

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