Water → HCID 20230497, compound

HRID 2290818Notes

Reaction equation

HRID 2290818 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:11](=[O:18])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH:5]=[CH:6][C:7]=1[OH:8].[H-].[Na+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O>CN(C)C=O>[CH2:21]([O:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:11](=[O:18])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:2][CH:3]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl Bromide2×HCID 24758Sodium hydride2×HCID 13392885HCID 13392885, compound

Product 1

HCID 20230497HCID 20230497, compoundYield 174.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.2 g of 1-(3,4-dihydroxyphenyl)-3-nonanone in 10 ml of dimethylformamide was added 200 mg of oily sodium hydride (60%) and after stirring the mixture for 15 minutes at room temperature, 0.9 g of benzyl bromide was added to the mixture followed by stirring for 15 minutes at room temperature. After further adding thereto 200 mg of oily sodium hydride (60%) and stirring the mixture for 15 minutes at room temperature, 0.9 g of benzyl bromide was added to the mixture followed by stirring for 1.5 hours at room temperature. After adding 50 ml of water to the reaction mixture, the product was extracted with toluene. The extract was washed with water, dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was applied to silica gel column chromatography and eluted with toluene to provide 1.8 g of 1-(3,4-dibenzyloxyphenyl)-3-nonanone as a sticky product.

Workup

  1. stirringby stirring for 15 minutes at room temperature
  2. additionAfter further adding
  3. stirringby stirring for 1.5 hours at room temperature
  4. extractionthe product was extracted with toluene
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. washeluted with toluene

Sources & evidence

ORD record
ord-200c6ac3278c4bc0adade3ff63b55a18
Source dataset
uspto-grants-1986_10
Patent number
US04618627

Reaction notes

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