Water → HCID 12043057, compound

HRID 1275031Notes

Reaction equation

HRID 1275031 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 placed 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 added to dichloromethane and stirred for 30 min. with a 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. additionThe residue was added to dichloromethane
  13. stirringstirred for 30 min. with a catalytic amount of p-toluenesulphonic acid (9 g)
  14. washThe dichloromethane layer was washed with sodium bicarbonate solution
  15. customdried
  16. customThe residue was crystallized from diisopropylether

Sources & evidence

ORD record
ord-c5f4788af41d49aa98cd93cec8e70ae6
Source dataset
uspto-grants-2000_12
Patent number
US06159988

Reaction notes

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