Ethylene Glycol → HCID 86709937, compound

HRID 1526768Notes

Reaction equation

HRID 1526768 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)[CH:5]=[O:6].[CH2:14](O)[CH2:15][OH:16]>C1(C)C=CC=CC=1.CCOC(C)=O.CC1C=CC(S(O)(=O)=O)=CC=1.O>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]2[O:16][CH2:15][CH2:14][O:6]2)[CH:7]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:9]=1

Participants

6

Reactant 2

HCID 174Ethylene GlycolHCID 161154383-Bromo-5-(trifluoromethyl)benzaldehyde

Product 1

HCID 86709937HCID 86709937, compoundYield 85.2%

Reagents, catalysts & solvents 3

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-bromo-5-trifluoromethyl benzaldehyde (10 gm, 39.523 mmol), ethylene glycol (6.63 ml, 118.568 mmol) and PTSA.H2O (150 mg, 0.79 mmol) in anhydrous toluene (60 ml) was heated to reflux under Dean-stark conditions for 6 h. The reaction mixture was diluted with EtOAc (100 ml) and washed with water (150 ml) and brine solution (150 ml). Organic layer was dried over Na2SO4, filtered and evaporated in vacuum to afford 11 g crude as a colorless liquid which was purified by column chromatography (100-200 silica gel mesh), eluted with 5% EtOAc in Hexane to afford the desired compound (10 g) as a colorless liquid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under Dean-stark conditions for 6 h
  3. washwashed with water (150 ml) and brine solution (150 ml)
  4. dry with materialOrganic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated in vacuum
  7. customto afford 11 g crude as a colorless liquid which
  8. customwas purified by column chromatography (100-200 silica gel mesh)
  9. washeluted with 5% EtOAc in Hexane

Sources & evidence

ORD record
ord-3bfe2341cce94214a030c7951352ab3e
Source dataset
uspto-grants-2015_07
Patent number
US09085606B2

Reaction notes

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