Ethylene Glycol → 2-(3-Bromo-4-methoxyphenyl)-1,3-dioxolane

HRID 1662743노트

반응식

HRID 1662743 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6].[CH2:12](O)[CH2:13][OH:14].C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>C1C=CC=CC=1.O>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]2[O:14][CH2:13][CH2:12][O:6]2)[CH:7]=[CH:8][C:9]=1[O:10][CH3:11]

참가 물질

7

반응물 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 986623-Bromo-4-methoxybenzaldehydeHCID 516892Sodium Bicarbonate

생성물 1

HCID 179350472-(3-Bromo-4-methoxyphenyl)-1,3-dioxolane수율 92.6%

시약·촉매·용매 2

HCID 241Benzene용매HCID 962Water용매

실험 절차

A solution of 53.0 g of 3-bromo-4-methoxy benzaldehyde, 18.4 g of ethylene glycol, and 4.24 g of p-toluene sulfonic acid/1 hydrate in benzene was refluxed for 5 hours while taking water out of the system. After the mixture was cooled, the reaction solution was poured into a saturated aqueous solution of NaHCO3, liquid separation was performed, and the aqueous layer was extracted with benzene. The combined organic layer was washed with saturated brine and dried over MgSO4, then, the drying agent was separated by filtration and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography (Chromatorex NH; mobile phase: EtOAc/n-hexane=1/9; v/v) to obtain 59.1 g of the title compound (colorless oil) was obtained.

후처리

  1. temperatureAfter the mixture was cooled
  2. extractionthe aqueous layer was extracted with benzene
  3. washThe combined organic layer was washed with saturated brine
  4. dry with materialdried over MgSO4
  5. customthe drying agent was separated by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe obtained residue was purified by column chromatography (Chromatorex NH; mobile phase: EtOAc/n-hexane=1/9; v/v)

출처 및 근거

ORD 기록
ord-db12b2397d474176af4247f789900e6a
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030499B2

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