2,4,6-Cycloheptatrien-1-one, 3-bromo-2-hydroxy- → HCID 439776, compound

HRID 1438884Notes

Reaction equation

HRID 1438884 reaction equation
Br[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4](=[O:9])[C:3]=1[OH:10].[CH3:11][O-:12].[Na+].[Na]>CO>[OH:10][C:3]1[C:4](=[O:9])[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[O:12][CH3:11]

Participants

5

Reactant 3

HCID 207182,4,6-Cycloheptatrien-1-one, 3-bromo-2-hydroxy-HCID 5360545SodiumHCID 10942334Sodium Methoxide

Product 1

HCID 439776HCID 439776, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 3-bromo-2-hydroxy-2,4,6-cycloheptatrien-1-one [27.5 g, described by T. Toda et al., Nippon Hagaku Zasshi, 88, 1234-5 (1967), (CA 68 101342)] and sodium methoxide (prepared from 12.6 g of sodium in methanol followed by evaporation of the methanol) in dimethyl sulfoxide (300 ml) is heated at 80° C for 1 hour. The solution is cooled poured on ice, acidified with 2N sulfuric acid and extracted with ethyl acetate. The organic extract is washed with brine, dried over sodium sulfate and evaporated. The residue is crystallized from ethyl acetate-hexane to give 2-hydroxy-3-methoxy-2,4,6-cycloheptatrien-1-one. Evaporation of the mother liquors gives 2-hydroxy-4-methoxy-2,4,6-cycloheptatrien-1-one.

Workup

  1. customfollowed by evaporation of the methanol) in dimethyl sulfoxide (300 ml)
  2. temperatureThe solution is cooled
  3. additionpoured on ice
  4. extractionextracted with ethyl acetate
  5. extractionThe organic extract
  6. washis washed with brine
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. customThe residue is crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-acdfbdd3a5734445a3bb163cad0b317f
Source dataset
uspto-grants-1977_11
Patent number
US04057556

Reaction notes

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