Water → HCID 12043057, compound

HRID 1955744Notes

Reaction equation

HRID 1955744 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[C:5]([O:11][CH3:12])[C:4]=1Br.[C:14]1(=O)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.O>O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[C:5]([O:11][CH3:12])[C:4]=1[C:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7967CyclohexanoneHCID 708022-Bromo-1,3,5-trimethoxybenzene

Product 1

HCID 12043057HCID 12043057, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-30 °C

Procedure

2,4,6-Trimethoxybromobenzene (1 eqvt.) was taken in a flame dried 3-necked flask under nitrogen. Dry tetrahydrofuran (THF) (983 ml) was added and the reaction mixture was cooled to -30° C. n-BuLi (1.3 eqvt.) in hexane (commercial) was added dropwise and after the addition the reaction mixture was stirred for 30 min. Thin layer chromatographic examination at this stage indicated completion of metallation reaction. Cyclohexanone (1.1 eqvt.) diluted with equal volume of dry THF was added to the reaction mixture at -30° C. and the reaction mixture was stirred for another one hour at -30° C. and later allowed to come to room temperature. Water (150 ml) was added and extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated. The residue was taken in dichloromethane and stirred for 30 min. with catalytic amount of p-toluenesulphonic acid (9 g). The dichloromethane layer was washed with sodium bicarbonate solution followed by water and dried. The residue was crystallized from Diisopropylether to give the title compound; m.p. 127° C., Yield: 64.7%.

Workup

  1. customdried 3-necked flask under nitrogen
  2. additionDry tetrahydrofuran (THF) (983 ml) was added
  3. additionwas added dropwise
  4. additionafter the addition the reaction mixture
  5. customcompletion of metallation reaction
  6. additionwas added to the reaction mixture at -30° C.
  7. stirringthe reaction mixture was stirred for another one hour at -30° C.
  8. customto come to room temperature
  9. extractionextracted with ethyl acetate
  10. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  11. concentrationconcentrated
  12. stirringstirred for 30 min. with catalytic amount of p-toluenesulphonic acid (9 g)
  13. washThe dichloromethane layer was washed with sodium bicarbonate solution
  14. customdried
  15. customThe residue was crystallized from Diisopropylether

Sources & evidence

ORD record
ord-9f4a21356a9e4ffaae9a2ef6a0a8c4f0
Source dataset
uspto-grants-1998_07
Patent number
US05776977

Reaction notes

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