1-Butanol → 2-(Bromomethyl)-2-(3-bromo-4-methylphenyl)-1,3-dioxolane

HRID 971638Notes

Reaction equation

HRID 971638 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][C:7]=1[CH3:8].[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:4]2[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([Br:1])[CH:3]=2)[O:16][CH2:12][CH2:13][O:11]1

Participants

8

Reactant 4

HCID 2631-ButanolHCID 6101p-Toluenesulfonic acidHCID 24408BromineHCID 33094011-(3-Bromo-4-methylphenyl)ethan-1-one

Product 1

HCID 126225002-(Bromomethyl)-2-(3-bromo-4-methylphenyl)-1,3-dioxolaneYield 57%

Reagents, catalysts & solvents 3

HCID 174Ethylene GlycolSolventHCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

To a stirred and hot (50° C.) solution of 64 parts of 1-(3-bromo-4-methylphenyl)-1-ethanone in 160 parts of 1-butanol are added dropwise, during a 1 hour-period, 48 parts of bromine without external heating. After stirring for 1 hour at room temperature, there are added successively 21.7 parts of 1,2-ethanediol, 6 parts of 4-methylbenzenesulfonic acid and 720 parts of benzene. The whole is stirred and refluxed overnight with water-separator. The reaction mixture is evaporated and the residue is taken up in 2,2'-oxybispropane. The resulting solution is washed successfully once with a diluted sodium hydroxide solution and three times with water, dried, filtered and evaporated. The residue is distilled, yielding 57 parts (57%) of 2-(bromomethyl)-2-(3-bromo-4-methylphenyl)-1,3-dioxolane; bp. 126°-130° C. at 0.1 mm. pressure.

Workup

  1. stirringAfter stirring for 1 hour at room temperature
  2. stirringThe whole is stirred
  3. customThe reaction mixture is evaporated
  4. washThe resulting solution is washed successfully once 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-455c853dfc214f9882d7a3b20107f510
Source dataset
uspto-grants-1979_07
Patent number
US04160838

Reaction notes

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