Trimethylhydroquinone → 2,5-Cyclohexadiene-1,4-dione, 2,3,5-trimethyl-

HRID 482525

반응식

HRID 482525 반응식
[CH3:1][C:2]1[C:3]([OH:11])=[C:4]([CH3:10])[C:5]([CH3:9])=[C:6]([CH:8]=1)[OH:7]>O.CC(C)=O>[CH3:1][C:2]1[C:3](=[O:11])[C:4]([CH3:10])=[C:5]([CH3:9])[C:6](=[O:7])[CH:8]=1

참가 물질

4

반응물 1

HCID 12785Trimethylhydroquinone

생성물 1

HCID 702912,5-Cyclohexadiene-1,4-dione, 2,3,5-trimethyl-수율 85.6%

시약·촉매·용매 2

HCID 180Acetone용매HCID 962Water용매

실험 절차

A suspension of 25.6 g of ferric chloride in 50 ml of water was added at room temperature to a solution of 20 g of trimethylhydroquinone in 150 ml of acetone, and the resulting mixture was stirred for 1 hour, after which it was allowed to stand for 2 days. At the end of this time, it was concentrated to about one half of its original volume, and the concentrate was mixed with water. The resulting aqueous mixture was extracted with ethyl acetate, and the extract was washed with water and with a saturated aqueous solution of sodium chloride, in that order, after which it was dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel, using a 1:6 by volume mixture of ethyl acetate and hexane as the eluent, to give 16.9 g of the title compound having an Rf value=0.48 (on thin layer chromatography on silica gel; developing solvent: a 1:6 by volume mixture of ethyl acetate and hexane).

후처리

  1. waitto stand for 2 days
  2. concentrationAt the end of this time, it was concentrated to about one half of its original volume
  3. additionthe concentrate was mixed with water
  4. extractionThe resulting aqueous mixture was extracted with ethyl acetate
  5. washthe extract was washed with water and with a saturated aqueous solution of sodium chloride, in that order
  6. dry with materialafter which it was dried over anhydrous sodium sulfate
  7. customThe solvent was removed by distillation under reduced pressure
  8. customthe resulting residue was purified by column chromatography through silica gel
  9. additionby volume mixture of ethyl acetate and hexane as the eluent

출처 및 근거

ORD 기록
ord-e9212d1e200843caaf90372d25ae5f46
출처 데이터셋
uspto-grants-1998_08
특허 번호
US05798375

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