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

HRID 1870536Notes

Reaction equation

HRID 1870536 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.[CH2:11](O)[CH2:12][OH:13].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([CH3:9])[O:13][CH2:12][CH2:11][O:10]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 165023'-Bromoacetophenone

Product 1

HCID 109992182-(3-Bromophenyl)-2-methyl-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

1-(3-bromophenyl)ethanone (60.6 g), ethylene glycol (83.7 mL), and p-toluenesulfonic acid (0.15 g) were dissolved in benzene (250 mL) and heated at reflux overnight in a Dean-Stark apparatus. The mixture was cooled and washed with water. The aqueous layer was further extracted twice with chlorobutane and the combined organic layers were dried (MgSO4), filtered and the solvent was removed under reduced pressure to yield 75.0 g of a yellow oil. The oil was purified by distillation under reduced pressure (19-24 Pa, 64-74° C.) to afford 70.1 g of the title compound of Step A as an oil. 1H NMR (CDCl3): δ 7.64 (s,1H), 7.40 (m,2H), 7.20 (m,1H), 4.0 (m,2H), 3.7 (m,2H), 1.63 (s,3H).

Workup

  1. temperatureheated
  2. temperatureat reflux overnight in a Dean-Stark apparatus
  3. temperatureThe mixture was cooled
  4. washwashed with water
  5. extractionThe aqueous layer was further extracted twice with chlorobutane
  6. dry with materialthe combined organic layers were dried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ab50044f3c3c4fad99eb32f5fed0db93
Source dataset
uspto-grants-2000_08
Patent number
US06096895

Reaction notes

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