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

HRID 2257825Notes

Reaction equation

HRID 2257825 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

2.0 gm of 5-methoxy-8-nitro-1-tetralone (described in Japanese Patent Laid-open (ko-kai) 279891/1989) 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.

Workup

  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. custom(4:1) as an eluant to obtain fractions
  17. additioncontaining the target compound
  18. concentrationThe fractions were concentrated

Sources & evidence

ORD record
ord-4f4d83e887a94613a497a7b3b05d9c77
Source dataset
uspto-grants-1997_08
Patent number
US05658920

Reaction notes

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