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

HRID 2052380Notes

Reaction equation

HRID 2052380 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 Kagaku 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 one 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-1e0a74d6ca0140f8ba552f5566d65d7d
Source dataset
uspto-grants-1980_01
Patent number
US04183955

Reaction notes

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