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

HRID 1274215Notes

Reaction equation

HRID 1274215 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[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:3]=[C:4]([CH:5]2[O:12][CH2:11][CH2:10][O:6]2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 765833-Bromobenzaldehyde

Product 1

HCID 873062-(3-Bromophenyl)-1,3-dioxolaneYield 100.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 3-bromobenzaldehyde (5.00 g, 27.0 mmol) in toluene (35 ml) was added ethylene glycol (4.52 ml, 81.1 mmol) and p-toluenesulphonic acid (0.5 g). The mixture was heated to reflux for 2 hours, cooled, and washed with water and saturated sodium hydrogen carbonate solution. The organic layer was dried over MgSO4. The solvent was removed under reduced pressure to give the desired product as a colourless oil (6.22 g, 100%). δH (CDCl3) 4.09 (4H, m), 5.79 (1H, s), 7.2-7.7 (4H) ppm.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 hours
  3. temperaturecooled
  4. washwashed with water and saturated sodium hydrogen carbonate solution
  5. dry with materialThe organic layer was dried over MgSO4
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-29826425134847518dc54a5ed791944f
Source dataset
uspto-grants-2000_12
Patent number
US06156774

Reaction notes

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