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

HRID 249220Notes

Reaction equation

HRID 249220 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.[Cl-].[Al+3].[Cl-].[Cl-].[C:19](Cl)(=[O:21])[CH3:20].Cl>C(=S)=S>[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)ethanoneYield 96.5%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

To a solution of 3.00 g (16.6 mM) of 9,10-dihydrophenanthrene in 40 ml of dry carbon disulfide, 2.73 g (20.5 mM) of anhydrous aluminum chloride was added while being cooled on an ice-common salt bath. Under cooling on the bath, 1.27 ml (17.9 mM) of acetylchloride was gradually added dropwise to the mixture at -4° to -2° C., followed by stirring for 1 hour and 30 minutes at room temperature without cooling on the bath. After the reaction, the reaction mixture was poured into a mixture of 50 g of ice and 15 ml of hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with water, dried with anhydrous sodium sulfate, and distilled-off the solvent under reduced pressure to obtain 3.57 g of oily 2-acetyl-9,10-dihydrophenanthrene (Yield: 96.5%).

Workup

  1. temperaturewhile being cooled on an ice-common salt bath
  2. additionwas gradually added dropwise to the mixture at -4° to -2° C.
  3. temperaturewithout cooling on the bath
  4. customAfter the reaction
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materialdried with anhydrous sodium sulfate

Sources & evidence

ORD record
ord-56293f84bafa4dff8d3964deaae7fed5
Source dataset
uspto-grants-1993_05
Patent number
US05213709

Reaction notes

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