Benzene → 2,6-Dimethoxy-4-methylidenecyclohexa-2,5-dien-1-one

HRID 2296522노트

반응식

HRID 2296522 반응식
[CH3:1][O:2][C:3]1[C:4](=[O:14])[C:5]([O:12][CH3:13])=[CH:6][C:7](OC)([CH3:9])[CH:8]=1.C1C=CC=CC=1.C(=O)([O-])O.[Na+]>S(=O)(=O)(O)O>[CH3:13][O:12][C:5]1[C:4](=[O:14])[C:3]([O:2][CH3:1])=[CH:8][C:7](=[CH2:9])[CH:6]=1

참가 물질

5

반응물 3

HCID 241BenzeneHCID 516892Sodium BicarbonateHCID 13229516HCID 13229516, 화합물

생성물 1

HCID 132295172,6-Dimethoxy-4-methylidenecyclohexa-2,5-dien-1-one

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매

실험 절차

A 198 mg quantity of 2,4,6-trimethoxy-4-methyl-2,5-cyclohexadienone and 10 ml of benzene were dissolved in 10 ml of concentrated sulfuric acid, and stirred at room temperature for 2 hours. Thereafter the solution was neutralized by adding sodium hydrogen carbonate to the solution and filtered. The filtrate was concentrated at reduced pressure. The residue was extracted with dichloromethane, the solvent was removed at reduced pressure and the resulting residue was concentrated, thereby recovering 158 mg of an oily crude product. The crude product was purified by silica gel column chromatography using a 20:1 benzene-ethyl acetate mixture, giving 153 mg of 2,6-dimethoxy-4-methylidene-2,5-cyclohexadienone in 92% of theoretical yield. The compound thus obtained was identified by NMR.

후처리

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated at reduced pressure
  3. extractionThe residue was extracted with dichloromethane
  4. customthe solvent was removed at reduced pressure
  5. concentrationthe resulting residue was concentrated
  6. customrecovering 158 mg of an oily crude product
  7. customThe crude product was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-8d0744d77658420cadd02b6f08e3bd90
출처 데이터셋
uspto-grants-1984_01
특허 번호
US04429164

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