Water → HCID 10445672, compound

HRID 654700Notes

Reaction equation

HRID 654700 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[OH:12].[H-].[Na+].[CH3:15][O:16][CH2:17]Cl.O>CN(C)C=O>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[O:12][CH2:15][O:16][CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 123363945-Bromonaphthalen-1-ol

Product 1

HCID 10445672HCID 10445672, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6.0 g of 5-bromo-1-naphthol was dissolved in 50 ml of N,N-dimethylformamide, to which 1.2 g of 60% sodium hydride was added. After stirring at a room temperature for 10 min, it was cooled to 0° C., to which 3.5 ml of chloromethyl methyl ether was added and stirred for 10 min. Water was added to the reaction solution, which was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and then the solvent was distilled off. When the resultant residue was purified on silica gel column chromatography (10% ethyl acetate/hexane), 7.2 g of the above-captioned compound was obtained as red acicular crystals.

Workup

  1. additionwas added
  2. additionwas added
  3. stirringstirred for 10 min
  4. extractionwas extracted with ethyl acetate
  5. washThe extract was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off
  8. customWhen the resultant residue was purified on silica gel column chromatography (10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d5b6a128a01945bc982a47df6cf78465
Source dataset
uspto-grants-1992_07
Patent number
US05134111

Reaction notes

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