Ethylene Glycol → HCID 22012609, compound

HRID 1533123Notes

Reaction equation

HRID 1533123 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[CH2:10](O)[CH2:11][OH:12]>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[F:1][C:2]1[CH:3]=[C:4]([CH:5]2[O:12][CH2:11][CH2:10][O:6]2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 174Ethylene GlycolHCID 680093-Fluorobenzaldehyde

Product 1

HCID 22012609HCID 22012609, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 3-fluorobenzaldehyde (3.0 g, 24.2 mmol) in toluene (100 ml) was treated with ethylene glycol (1.8 g, 29.0 mmol) and p-toluenesulfonic acid (0.05 g, 0.24 mmol). The resulting solution was stirred at 80° C. for 3 hours. The reaction solution was partitioned between ethyl acetate and water. The organic layer was washed (brine), dried (Na2SO4), filtered, and concentrated under vacuum. The residue was purified on silica gel using 10% ethyl acetate/hexane to provide the title compound (3.4 g, 85%).

Workup

  1. customThe reaction solution was partitioned between ethyl acetate and water
  2. washThe organic layer was washed (brine)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified on silica gel using 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-06e609d17c4342149a93f63b00613f39
Source dataset
uspto-grants-2001_03
Patent number
US06207701B1

Reaction notes

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