Trifluoroacetic acid → 1-Benzylnaphthalene

HRID 1275419

Reaction equation

HRID 1275419 reaction equation
[H-].[Na+].FC(F)(F)C(O)=O.[C:10]([C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1)(=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(Cl)Cl>[CH2:10]([C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 24758Sodium hydride2×HCID 695031-Benzoylnaphthalene

Product 1

HCID 380741-BenzylnaphthaleneYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sodium hydride pellets (98% NaH; 3.5 g; 5.3 eq) were added to 50 mL of trifluoroacetic acid at ice-water bath temperature, under nitrogen atmosphere. 1-Benzoylnaphthalene (4.0 g; 17.2 mMol), as prepared above, in 25 mL of methylene chloride, was added dropwise. The mixture was allowed to stir overnight while warming to room temperature. The mixture was poured onto ice, the layers were separated, and the aqueous layer was extracted with methylene chloride. The combined organic extractions were washed with saturated sodium bicarbonate, and brine; then dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to medium pressure chromatography on silica gel, eluting with ethyl acetate:hexane/5:95. The desired product was obtained as a white powder (3.0 g; 80% yield).

Workup

  1. additionwas added dropwise
  2. additionThe mixture was poured onto ice
  3. customthe layers were separated
  4. extractionthe aqueous layer was extracted with methylene chloride
  5. extractionThe combined organic extractions
  6. washwere washed with saturated sodium bicarbonate, and brine
  7. dry with materialthen dried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-6dfee91f698e424397b6aea4b123dbde
Source dataset
uspto-grants-2000_12
Patent number
US06160175

Linked notes

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