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

HRID 2228385Notes

Reaction equation

HRID 2228385 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH2:10](O)[CH2:11][OH:12].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]2[O:12][CH2:11][CH2:10][O:7]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 707414-Bromobenzaldehyde

Product 1

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

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 4-bromobenzaldehyde (1 Scheme 18, 9.5 g, 51.4 mmol) and ethylene glycol (6.4 g, 113 mmol) and p-toluenesulfonic acid (120 mg) in benzene (200 mL) was refluxed in a Dean Stark apparatus for 4 h. The reaction mixture was cooled to room temperature, and the solution was extracted with cold water/ethyl acetate. The organic layer was washed with brine, dried (Na2SO4), and concentrated to give a colorless oil (11.4, 95%); 1H NMR (300 MHz, CDCl3) δ 4.01-4.14 (4 H), 5.78 (s, 1 H), 7.37 (d, J=8.34 Hz, 2 H), 7.53 (d, J=8.34 Hz, 2 H); HRMS (EI) calcd for C9H9BrO2 227.9786, 229.9766, found 227.9771, 229.9754.

Workup

  1. temperaturewas refluxed in a Dean Stark apparatus for 4 h
  2. extractionthe solution was extracted with cold water/ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customto give a colorless oil (11.4, 95%)

Sources & evidence

ORD record
ord-1f92a98fbc81452cbcd3e3a85552d76e
Source dataset
uspto-grants-2002_07
Patent number
US06416861B1

Reaction notes

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