Chloroform → 4-Hydroxy-5-methoxy-8-nitro-1-tetralone

HRID 964644노트

반응식

HRID 964644 반응식
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][C:8]2=[O:16].C(OOC(=O)C1C=CC=CC=1)(=[O:24])C1C=CC=CC=1.C(Cl)(Cl)Cl>C(Cl)(Cl)(Cl)Cl>[OH:24][CH:5]1[C:4]2[C:9](=[C:10]([N+:13]([O-:15])=[O:14])[CH:11]=[CH:12][C:3]=2[O:2][CH3:1])[C:8](=[O:16])[CH2:7][CH2:6]1

참가 물질

5

반응물 3

HCID 6212ChloroformHCID 7187Benzoyl PeroxideHCID 150092155-Methoxy-8-nitro-1-tetralone

생성물 1

HCID 224495374-Hydroxy-5-methoxy-8-nitro-1-tetralone

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

2.0 gm of 5-methoxy-8-nitro-1-tetralone (described in Japanese Patent Laid-open (ko-kai) 279891/1989 and also in U.S. Pat. No. 4,939,255) and 2.05 gm of N-bromosuccinic imide were dissolved in 50 ml of carbon tetrachloride. After the addition of a catalytic amount of benzoyl peroxide, the mixture was heated under reflux for 4 hours and then cooled to room temperature, followed by the addition of 50 ml of chloroform. The mixture was washed with 10% aqueous solution of sodium hydroxide, water, and saturated brine in this order, and dried over anhydrous sodium sulfate. To the residue obtained by removing the solvent were added 5 ml of tetrahydrofuran, 5 ml of ethanol, 8 ml of water, and 250 mg of calcium carbonate, and the mixture was heated under reflux. A residue was obtained by removing the solvent from the reaction mixture, which, after the addition of 50 ml of water, was extracted with chloroform. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and subjected to silica gel column chromatography using chloroform-ethyl acetate (4:1) as an eluant to obtain fractions containing the target compound. The fractions were concentrated to produce 1.49 gm of light yellow powder of the title compound.

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. washThe mixture was washed with 10% aqueous solution of sodium hydroxide, water, and saturated brine in this order
  4. dry with materialdried over anhydrous sodium sulfate
  5. customTo the residue obtained
  6. customby removing the solvent
  7. additionwere added 5 ml of tetrahydrofuran, 5 ml of ethanol, 8 ml of water, and 250 mg of calcium carbonate
  8. temperaturethe mixture was heated
  9. temperatureunder reflux
  10. customA residue was obtained
  11. customby removing the solvent from the reaction mixture, which
  12. additionafter the addition of 50 ml of water
  13. extractionwas extracted with chloroform
  14. washThe extract was washed with saturated brine
  15. dry with materialdried over anhydrous sodium sulfate
  16. customto obtain fractions
  17. additioncontaining the target compound
  18. concentrationThe fractions were concentrated

출처 및 근거

ORD 기록
ord-62fa538c6d1c41cca2ded53d95839964
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05770605

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