Toluene → HCID 66692910, compound

HRID 2367983Notes

Reaction equation

HRID 2367983 reaction equation
[Br:1][C:2]1[C:9]([O:10][CH2:11][CH3:12])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C1(C)C=CC(S(O)(=O)=[O:20])=CC=1.[C:24]1([CH3:30])C=CC=CC=1>>[Br:1][C:2]1[C:9]([O:10][CH2:11][CH3:12])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]1[O:20][CH2:24][CH2:30][O:5]1

Participants

4

Reactant 3

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 86664737HCID 86664737, compound

Product 1

HCID 66692910HCID 66692910, compoundYield 86%

Procedure

To a solution of 2-bromo-3-ethoxybenzaldehyde (128 g, 0.56 mol) and glycol (253 mL, 4.49 mol) in toluene (600 mL) was added p-toluenesulfonic acid (10 g, 0.06 mol). The reaction flask had a Dean and Stark condenser attached and the reaction mixture was refluxed to remove the water for 4 h. The reaction mixture was then cooled to room temperature and concentrated in vacuo. The residue was purified by column chromatography on silica gel to give the target compound (132 g, yield 86%).

Workup

  1. temperaturethe reaction mixture was refluxed
  2. customto remove the water for 4 h
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-77b0228eeb964fa9ada9f50e33e470ae
Source dataset
uspto-grants-2014_04
Patent number
US08703742B2

Reaction notes

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