Water → HCID 14986461, compound

HRID 654693Notes

Reaction equation

HRID 654693 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[CH3:12])[CH:5]=[CH:4][C:3]=1[C:13](=[O:15])[CH3:14].[H-].[Na+].[CH2:18](Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CN(C)C=O>[CH2:18]([O:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[CH3:12])[CH:5]=[CH:4][C:3]=1[C:13](=[O:15])[CH3:14])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 14986460HCID 14986460, compound

Product 1

HCID 14986461HCID 14986461, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

5.5 g of 1'-hydroxy-8'-methyl-2'-acetonaphthone was dissolved in 50 ml of N,N-dimethylformamide, to which 1.7 g of 60% sodium hydride was added, followed by agitation at 50° C. for 10 minutes. The reaction solution was returned to room temperature, in which 5.5 ml of benzyl chloride was dropped, followed by heating again to 70° C. for reaction for 1 hour. After returning to room temperature, water was added to the solution, which was extracted with ethyl acetate. The resultant organic phase was washed with a saturated saline solution, dried with anhydrous magnesium sulfate and concentrated under reduced pressure. The resultant reside was purified by silica gel column chromatography (15% ethyl acetate/hexane) to obtain 4.8 g of the captioned compound as a brown oily substance.

Workup

  1. additionwas added
  2. additionwas dropped
  3. customAfter returning to room temperature
  4. extractionwas extracted with ethyl acetate
  5. washThe resultant organic phase was washed with a saturated saline solution
  6. dry with materialdried with anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resultant reside was purified by silica gel column chromatography (15% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-7043e3acde144139a640779b7002a53c
Source dataset
uspto-grants-1992_07
Patent number
US05134111

Reaction notes

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