Ethylene Glycol → 773102-28-6

HRID 716017Notes

Reaction equation

HRID 716017 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].[F:5][C:6]1[C:13]([F:14])=[C:12]([F:15])[CH:11]=[CH:10][C:7]=1[CH:8]=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[F:5][C:6]1[C:13]([F:14])=[C:12]([F:15])[CH:11]=[CH:10][C:7]=1[CH:8]1[O:4][CH2:1][CH2:2][O:3]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 5192262,3,4-TrifluorobenzaldehydeHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 86727231773102-28-6

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Ethylene glycol (348.7 g, 5.62 mol) was added in one portion to a stirred mixture of 2,3,4-trifluorobenzaldehyde (300.0 g, 1.87 mol) and p-toluenesulfonic acid monohydrate (35.6 g, 0.18 mol) in toluene (4.5 L) at ambient temperature. The resulting mixture was heated at reflux with azeotropic removal of water using a Dean-Stark apparatus. The water was removed from time to time (3 hour intervals). After 24 hours, the toluene was removed and the residue was diluted with ethyl acetate (1.5 L) and washed with saturated aqueous NaHCO3 (2×750 mL), water (2×500 mL) and brine solution (500 mL). The organic layers were dried over sodium sulphate and the solvent was removed under vacuum. The crude product was subjected to distillation at 60-70° C. in high vacuum (0.1 mm of Hg) to remove the starting material and impurities. The fraction obtained at 75-85° C. (0.1 mm of Hg) is consistent the title compound. Yield: 300.0 g (78%). 1H NMR (400 MHz, DMSO-d6) δ: 3.9-4.1 (m, 4H), 6.0 (s, 1H), 7.3-7.4 (m, 2H).

Workup

  1. temperatureThe resulting mixture was heated
  2. customThe water was removed from time to time (3 hour intervals)
  3. customthe toluene was removed
  4. additionthe residue was diluted with ethyl acetate (1.5 L)
  5. washwashed with saturated aqueous NaHCO3 (2×750 mL), water (2×500 mL) and brine solution (500 mL)
  6. dry with materialThe organic layers were dried over sodium sulphate
  7. customthe solvent was removed under vacuum
  8. distillationThe crude product was subjected to distillation at 60-70° C. in high vacuum (0.1 mm of Hg)
  9. customto remove the starting material and impurities
  10. customThe fraction obtained at 75-85° C. (0.1 mm of Hg)

Sources & evidence

ORD record
ord-9f98bb63360a43ae821ff66a05735101
Source dataset
uspto-grants-2015_11
Patent number
US09187495B2

Reaction notes

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