1-Butanol → 2-(Bromomethyl)-2-(2,3-dichlorophenyl)-1,3-dioxolane

HRID 263047Notes

Reaction equation

HRID 263047 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].[CH2:12]([OH:16])[CH2:13]CC.[Br:17]Br.CC1C=CC(S(O)(=O)=O)=CC=1>O.C1C=CC=CC=1.C(O)CO>[Br:17][CH2:10][C:9]1([C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([Cl:8])[C:2]=2[Cl:1])[O:16][CH2:12][CH2:13][O:11]1

Participants

8

Reactant 4

HCID 2631-ButanolHCID 6101p-Toluenesulfonic acidHCID 24408BromineHCID 919861-(2,3-Dichlorophenyl)ethan-1-one

Product 1

HCID 126224812-(Bromomethyl)-2-(2,3-dichlorophenyl)-1,3-dioxolaneYield 49%

Reagents, catalysts & solvents 3

HCID 174Ethylene GlycolSolventHCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 120 parts of 1-(2,3-dichlorophenyl)-1-ethanone in 240 parts of butanol are added dropwise 101 parts of bromine at room temperature. After stirring for 1 hour at room temperature, there are added successively 42 parts of 1,2-ethanediol, 540 parts of anhydrous benzene and 4 parts of 4-methylbenzenesulfonic acid. The whole is stirred and refluxed overnight with water-separator. The reaction mixture is evaporated and the residue is dissolved in 2,2'-oxybispropane. The solution is washed with a diluted sodium hydroxide solution and three times with water, dried, filtered and evaporated. The residue is distilled, yielding 96.6 parts (49%) of 2-(bromomethyl)-2-(2,3-dichlorophenyl)-1,3-dioxolane; bp. 135°-137° C. at 0.1 mm. pressure.

Workup

  1. stirringThe whole is stirred
  2. customThe reaction mixture is evaporated
  3. dissolutionthe residue is dissolved in 2,2'-oxybispropane
  4. washThe solution is washed with a diluted sodium hydroxide solution and three times with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. distillationThe residue is distilled

Sources & evidence

ORD record
ord-7490623b319f4c5b88090fda0263ba4c
Source dataset
uspto-grants-1979_05
Patent number
US04156008

Reaction notes

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