Ethylene Glycol → HCID 22620058, compound

HRID 840599Notes

Reaction equation

HRID 840599 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH2:12](O)[CH2:13][OH:14].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[I:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH3:11])=[C:6]([CH:7]2[O:14][CH2:13][CH2:12][O:8]2)[CH:9]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 2622405-iodo-2-methoxybenzaldehyde

Product 1

HCID 22620058HCID 22620058, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1.0 grams (3.82 mmol) of the above aldehyde, 0.85 mL of ethylene glycol, 20 mg of p-toluenesulfonic acid and 42 mL of toluene was refluxed under nitrogen for 18 hours, cooled and concentrated in vacuo. The residue was redissolved in 50 mL of CH2Cl2, washed with saturated aqueous NaHCO3, dried over MgSO4 and concentrated to an oil. Chromatography on silica gel (10% ethyl acetate (EtOAc): 90% hexane) gave 2-(5-iodo-2-methoxyphenyl)-1,3-dioxolane as a clear oil, 0.68 grams (58%).

Workup

  1. temperaturecooled
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was redissolved in 50 mL of CH2Cl2
  4. washwashed with saturated aqueous NaHCO3
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated to an oil

Sources & evidence

ORD record
ord-3cc86c6c7df64bb8b1976b7747109236
Source dataset
uspto-grants-2002_04
Patent number
US06369074B1

Reaction notes

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