Ethylene Glycol → 2-(4-Bromophenyl)-1,3-dioxolane

HRID 277347

Reaction equation

HRID 277347 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:22](O)[CH2:23][OH:24].O>C1C=CC=CC=1.C(OCC)(=O)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]2[O:24][CH2:23][CH2:22][O:7]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 707414-BromobenzaldehydeHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 27738422-(4-Bromophenyl)-1,3-dioxolane

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Bromobenzaldehyde (3 g, 0.0162 mol) in benzene (60 mL) was treated with p-toluenesulfonic acid monohydrate (0.15 g, 0.79 mmol) and ethylene glycol (5 mL, 0.0896 mol). The reaction was refluxed under nitrogen with azeotropic removal of water. After 3 hours, the reaction was cooled to room temperature and diluted with an equal volume of ethyl acetate. This solution was washed twice with aqueous bicarbonate, dried over magnesium sulfate and concentrated under reduced pressure. A colorless oil was recovered. Yield=2.83 g (92%). TLC (5% ethyl acetate in hexanes) showed clean product, Rf=0.17.

Workup

  1. washThis solution was washed twice with aqueous bicarbonate
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customA colorless oil was recovered

Sources & evidence

ORD record
ord-84621f6afa09447c93b1caa0b9e5a63f
Source dataset
uspto-grants-2002_03
Patent number
US06355803B1

Linked notes

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