Ethylene Glycol → HCID 11666435, compound

HRID 1628004Notes

Reaction equation

HRID 1628004 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[CH2:11](O)[CH2:12][OH:13]>C1(C)C=CC=CC=1.CCOC(C)=O.S(O)(C1C=CC(C)=CC=1)(=O)=O.O>[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:9])[O:13][CH2:12][CH2:11][O:10]2)=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 174Ethylene GlycolHCID 728691-(4-Iodophenyl)ethan-1-one

Product 1

HCID 11666435HCID 11666435, compoundYield 99.1%

Reagents, catalysts & solvents 3

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

Procedure

1-(4-Iodophenyl)ethanone (15.0 g, 61 mmol) and ethylene glycol (7.17 g, 122 mmol) in toluene (120 mL) were treated with TsOH—H2O (0.290 g, 1.52 mmol). The flask was equipped with a Dean-Stark apparatus and condenser and heated to reflux for about 4 h. The mixture was cooled and concentrated under reduced pressure to give a material. The material was dissolved in EtOAc (120 mL) then washed with saturated aqueous NaHCO3 (25 mL) then saturated aqueous NaCl (30 mL). The organic layer was dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give 2-(4-iodophenyl)-2-methyl-1,3-dioxolane (17.54 g, 99%): LC/MS (Table 2, Method a) Rt=2.80 min; MS m/z 291 (M+H)+.

Workup

  1. customThe flask was equipped with a Dean-Stark apparatus and condenser
  2. temperatureheated
  3. temperatureto reflux for about 4 h
  4. temperatureThe mixture was cooled
  5. concentrationconcentrated under reduced pressure
  6. customto give a material
  7. washthen washed with saturated aqueous NaHCO3 (25 mL)
  8. dry with materialThe organic layer was dried over anhydrous MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-72432df4230b47758cfebb77db4f4fcc
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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