Hydrochloric Acid → 1-(9,10-Dihydrophenanthren-2-yl)ethanone

HRID 248045Notes

Reaction equation

HRID 248045 reaction equation
[CH:1]1[C:14]2[CH2:13][CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Al+3].[Cl-].[Cl-].[Cl-].[C:19](Cl)(=[O:21])[CH3:20].Cl>C(Cl)Cl>[C:19]([C:9]1[CH:8]=[CH:7][C:6]2[C:5]3[C:14](=[CH:1][CH:2]=[CH:3][CH:4]=3)[CH2:13][CH2:12][C:11]=2[CH:10]=1)(=[O:21])[CH3:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 130589,10-DihydrophenanthreneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 2202091-(9,10-Dihydrophenanthren-2-yl)ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 18 g (0.1 mole) 9,10-dihydrophenanthrene in 200 mL of dry CH2Cl2, cooled in ice, 20 g (0.15 mole) of anh. AlCl3 was added. To this solution 9.42 g (0.12 mmole) of acetyl chloride in 50 mL of dry CH2Cl2 was added in 17 mins. Stirring was continued for 30 mins in ice and 2 h at room temperature. The solution was poured on ice and 25 mL of concentrated HCl and stirred for 15 mins. The yellow organic layer was separated, washed with NaHCO3 solution, and dried. The solvent was removed and the residue distilled at 0.15 mm pressure. The distillate, 15.28 g, crystallized from ethanol-hexane, m.p. 58°-60° .

Workup

  1. stirringstirred for 15 mins
  2. customThe yellow organic layer was separated
  3. washwashed with NaHCO3 solution
  4. customdried
  5. customThe solvent was removed
  6. distillationthe residue distilled at 0.15 mm pressure
  7. customThe distillate, 15.28 g, crystallized from ethanol-hexane, m.p. 58°-60°

Sources & evidence

ORD record
ord-1790ae22345a43f0b5afc144ffbff6f8
Source dataset
uspto-grants-1993_05
Patent number
US05208263

Reaction notes

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