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

HRID 971639
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HRID 971639 반응식
[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:6]=1[CH3:12])=[O:4].[CH2:13]([OH:17])[CH2:14]CC.CC1C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>O.C(O)CO>[Br:1][CH2:2][C:3]1([C:5]2[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:6]=2[CH3:12])[O:17][CH2:13][CH2:14][O:4]1
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참가 물질

7

반응물 4

HCID 241BenzeneHCID 2631-ButanolHCID 6101p-Toluenesulfonic acidHCID 126225062-Bromo-1-(4-bromo-2-methylphenyl)ethanone

생성물 1

HCID 126267052-(Bromomethyl)-2-(4-bromo-2-methylphenyl)-1,3-dioxolane

시약·촉매·용매 2

HCID 174Ethylene Glycol용매
HCID 962
Water
용매

실험 절차

To a stirred mixture of 78.8 parts of 2-bromo-1-(4-bromo-2-methylphenyl)-1-ethanone and 200 parts of butanol are added 3 parts of 4-methylbenzenesulfonic acid and 225 parts of benzene. Then there are added dropwise 33.5 parts of 1,2-ethanediol. Upon completion, stirring is continued overnight at reflux temperature with water-separator. The reaction mixture is evaporated and the residue is dissolved in 2,2'-oxybispropane. The solution is stirred with 15 parts of a concentrated sodium hydroxide solution. The layers are separated and the aqueous phase is extracted with 2,2'-oxybispropane. The combined organic layers are washed with water (till neutralization), dried, filtered and evaporated. The solid residue is crystallized from methanol, yielding 30.5 parts of 2-(bromomethyl)-2-(4-bromo-2-methylphenyl)-1,3-dioxolane; mp. 86° C.

후처리

  1. customThe reaction mixture is evaporated
  2. dissolutionthe residue is dissolved in 2,2'-oxybispropane
  3. stirringThe solution is stirred with 15 parts of a concentrated sodium hydroxide solution
  4. customThe layers are separated
  5. extractionthe aqueous phase is extracted with 2,2'-oxybispropane
  6. washThe combined organic layers are washed with water (till neutralization)
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. customThe solid residue is crystallized from methanol

출처 및 근거

ORD 기록
ord-0011a136ac6744109d0f3add00245bf4
출처 데이터셋
uspto-grants-1979_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04160838

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