Water → 2-(4-Bromophenyl)-1,3-dioxolane

HRID 704687Notes

Reaction equation

HRID 704687 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[C:10]1([CH3:20])C=CC(S(O)(=O)=O)=CC=1.O.C([O-])([O-])=[O:23].[K+].[K+]>C1C=CC=CC=1.C(O)CO>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]2[O:23][CH2:10][CH2:20][O:7]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 11430Potassium CarbonateHCID 707414-Bromobenzaldehyde

Product 1

HCID 27738422-(4-Bromophenyl)-1,3-dioxolaneYield 70%

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 241BenzeneSolvent

Procedure

4-Bromobenzaldehyde (56 g, 0.3 mole) was dissolved in 500 mls of benzene containing 80 mls (excess) of ethylene glycol. This mixture was stirred rapidly via motor. p-Toluenesulfonic acid (5 g) was added and the mixture was refluxed with a water separator overnight (24 hours). The cooled mixture was poured into 1 liter of 5% K2CO3 and extracted with ethyl acetate. The organic phase was washed with H2O and then brine. The extract was dried over sodium sulfate and filtered. After solvent removal, the residue was chromatographed on silica gel using 10% ethyl acetate/hexane to give 50 g (70% yield.) of the title compound (m.p.=56°-57° C.).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with H2O
  3. dry with materialThe extract was dried over sodium sulfate
  4. filtrationfiltered
  5. customAfter solvent removal
  6. customthe residue was chromatographed on silica gel using 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-3f3c6b6ae0c947efbe9eefea2f5fa835
Source dataset
uspto-grants-1991_01
Patent number
US04988707

Reaction notes

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