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

HRID 129586

Reaction equation

HRID 129586 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH2:10](O)[CH2:11][OH:12]>C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]1[O:12][CH2:11][CH2:10][O:5]1

Participants

5

Reactant 2

HCID 174Ethylene GlycolHCID 811292-Bromobenzaldehyde

Product 1

HCID 5535342-(2-Bromophenyl)-1,3-dioxolaneYield 98.6%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 2-bromobenzaldehyde (100 g; 0.54 mol), ethylene glycol (67.03 g; 1.08 mol), p-toluenesulphonic acid (0.5 g) and toluene was heated to and maintained at reflux temperature for 6 hours. During this period, water/ethylene glycol (23 ml) was removed by azeotropic distillation. The mixture was cooled and ether (1 l) was added. The ether solution was washed with saturated sodium bicarbonate solution (200 ml) water (3×150 ml) and saturated brine (1×150 ml). After drying and filtration, evaporation of the ether solution gave 2-(2-bromophenyl)-1,3-dioxolane (121.96 g, 98.6% yield) as an oil.

Workup

  1. temperaturewas heated to and
  2. temperaturemaintained
  3. temperatureat reflux temperature for 6 hours
  4. waitDuring this period
  5. customwater/ethylene glycol (23 ml) was removed by azeotropic distillation
  6. temperatureThe mixture was cooled
  7. additionether (1 l) was added
  8. washThe ether solution was washed with saturated sodium bicarbonate solution (200 ml) water (3×150 ml) and saturated brine (1×150 ml)
  9. customAfter drying
  10. filtrationfiltration, evaporation of the ether solution

Sources & evidence

ORD record
ord-df3d23cae80f4fa2a29f02eb22d0e312
Source dataset
uspto-grants-1995_11
Patent number
US05468857

Linked notes

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