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

HRID 1074266Notes

Reaction equation

HRID 1074266 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

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-2368e5b914334b38a34dc9cca1e0f2d5
Source dataset
uspto-grants-1990_11
Patent number
US04973714

Reaction notes

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