Hydrofluoric Acid → 2-Phenyl-10-anthrone

HRID 68513Notes

Reaction equation

HRID 68513 reaction equation
C1C2C(=CC=CC=2)C=CC=1[C:11]1[CH:12]=[C:13]([CH:24]=[CH:25][CH:26]=1)[CH2:14][C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17]([OH:19])=O.F>>[C:11]1([C:11]2[CH:26]=[CH:25][C:24]3[C:17](=[O:19])[C:16]4[C:15](=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH2:14][C:13]=3[CH:12]=2)[CH:12]=[CH:13][CH:24]=[CH:25][CH:26]=1

Participants

3

Reactant 2

HCID 14917Hydrofluoric Acid2×HCID 58194347HCID 58194347, compound

Product 1

HCID 670655092-Phenyl-10-anthroneYield 144.7%

Procedure

First, 11.7 g of 2-[3-(2-naphthyl)benzyl]benzoic acid were added to 250 mL of liquid hydrogen fluoride, and then the mixture was stirred until hydrogen fluoride evaporated. The residue was dissolved in chloroform, and then the solution was sequentially washed with water, an aqueous solution of ammonium hydroxide, and water. After the chloroform solution had been dried with magnesium sulfate, the solvent was removed by distillation under reduced pressure. The residue was crystallized with methanol, and was then recrystallized with cyclohexane and acetone. Thus, 6.76 g of 2-phenyl-10-anthrone were obtained (in 61% yield).

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in chloroform
  3. washthe solution was sequentially washed with water
  4. dry with materialAfter the chloroform solution had been dried with magnesium sulfate
  5. customthe solvent was removed by distillation under reduced pressure
  6. customThe residue was crystallized with methanol
  7. customwas then recrystallized with cyclohexane and acetone

Sources & evidence

ORD record
ord-24756ba125c844d58954503471391797
Source dataset
uspto-grants-2014_09
Patent number
US08822041B2

Reaction notes

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