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

HRID 2228389Notes

Reaction equation

HRID 2228389 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][CH:5]=1)=[O:3].[CH2:11](O)[CH2:12][OH:13]>C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Br:10][C:7]1[CH:8]=[CH:9][C:4]([C:2]2([CH3:1])[O:13][CH2:12][CH2:11][O:3]2)=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 174Ethylene GlycolHCID 7466p-Bromoacetophenone

Product 1

HCID 6149202-(4-Bromophenyl)-2-methyl-1,3-dioxolaneYield 96%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 241BenzeneSolvent

Procedure

A mixture of 4-bromoacetophenone (1 Scheme 19, 20.0 g, 0.1 mol) and ethylene glycol (12.5 g, 0.2 mol) and p-toluenesulfonic acid (200 mg) in benzene (400 mL) was refluxed in a Dean Stark apparatus for 6 h. The reaction mixture was cooled to room temperature, and the solution was extracted with H2O/ethyl acetate. The organic layer was washed with brine, dried (Na2SO4), and concentrated to give a colorless oil (23 g, 96%); 1H NMR (300 MHz, CDCl3) δ 1.63 (s, 3 H), 3.76 (m, 2 H), 4.04 (m, 2 H), 7.37 (d, J=8.40 Hz, 2 H), 7.47 (d, J=8.40 Hz, 2 H); 13C NMR (75 MHz, CDCl3) 27.6, 64.5 (2C), 108.4, 121.9, 127.2 (2C), 131.4 (2C), 142.5

Workup

  1. temperaturewas refluxed in a Dean Stark apparatus for 6 h
  2. extractionthe solution was extracted with H2O/ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-16d6918e1d5a490cba749a3712db1c06
Source dataset
uspto-grants-2002_07
Patent number
US06416861B1

Reaction notes

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