Ethylene Glycol → HCID 21905308, compound

HRID 1247424Notes

Reaction equation

HRID 1247424 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH2:11](O)[CH2:12][OH:13].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]1[O:13][CH2:12][CH2:11][O:5]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 737702,4-Difluorobenzaldehyde

Product 1

HCID 21905308HCID 21905308, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred solution of 2,4-difluorobenzaldehyde (15.4 ml) in toluene (200 ml) was treated with ethylene glycol (23.2 ml) and p-toluene sulfonic acid (0.53 g). The reaction mixture was heated to reflux during 5 hrs (Dean-Stark trap), then it was cooled to r.t and poured onto ice. The organic layer was separated off, washed with 10% KHCO3-solution and brine, dried over MgSO4, filtered and concentrated to give 2-(2,4-difluoro-phenyl)-[1,3]dioxolane (26.8 g) as a light yellow oil. MS 186.1 ([M]+)

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux during 5 hrs (Dean-Stark trap)
  3. temperatureit was cooled
  4. additionpoured onto ice
  5. customThe organic layer was separated off
  6. washwashed with 10% KHCO3-solution and brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-507d461dad264b2bb1db601abe444d01
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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