Benzyl Bromide → 1-Benzyloxy-2-methyl-4-benzoyloxynaphthalene

HRID 277630Notes

Reaction equation

HRID 277630 reaction equation
[C:1]([O:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([OH:20])=[C:12]([CH3:21])[CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CC(C)=O>[CH2:28]([O:20][C:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10]([O:9][C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:11][C:12]=1[CH3:21])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 226254094-Benzoyloxy-2-methylnaphthol

Product 1

HCID 226254021-Benzyloxy-2-methyl-4-benzoyloxynaphthaleneYield 82.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

10.8 g (0.039 mol) of 4-benzoyloxy-2-methylnaphthol was dissolved in 100 ml of acetone, and to this was added 5.5 g (0.04 mol) of anhydrous potassium carbonate, and, while stirring at room temperature, 7.7 g (0.045 mol) of benzyl bromide was added dropwise over 30 minutes, and following completion of the addition, stirring was continued for 20 hours at room temperature. Then, inorganic salt was filtered out and the filtrate was concentrated under reduced pressure. The residue was extracted with ethyl acetate, washed with water, and the solvent evaporated under reduced pressure. n-Hexane was added to the residue to cause crystallization. Recrystallization from ethyl acetate-n-hexane gave 11.9 g of white crystals, m.p. 179-180° C.

Workup

  1. additioncompletion of the addition
  2. stirringstirring
  3. filtrationThen, inorganic salt was filtered out
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. extractionThe residue was extracted with ethyl acetate
  6. washwashed with water
  7. customthe solvent evaporated under reduced pressure
  8. additionn-Hexane was added to the residue
  9. customcrystallization
  10. customRecrystallization from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-f7e6f164531343acb99ce157251c25f6
Source dataset
uspto-grants-2002_03
Patent number
US06358515B2

Reaction notes

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