Hydrochloric Acid → 2-Acetylfluorene

HRID 2416350Notes

Reaction equation

HRID 2416350 reaction equation
[CH:1]1[C:13]2[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:18](Cl)(=[O:20])[CH3:19].Cl>ClCCl>[C:18]([C:9]1[CH:8]=[CH:7][C:6]2[C:5]3[C:13](=[CH:1][CH:2]=[CH:3][CH:4]=3)[CH2:12][C:11]=2[CH:10]=1)(=[O:20])[CH3:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 6853FluoreneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 699082-AcetylfluoreneYield 87.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A dichloromethane (1 L) solution of fluorene (150 g) was cooled down to 0° C., and anhydrous aluminum chloride (126 g) was added thereto little by little. Next, a dichloromethane (400 mL) solution of acetyl chloride (74 g) was dropwise added and stirred for one hour while maintaining 0° C. The reaction mixture was poured into 6M-hydrochloric acid (1 L) containing ice, and the solid matters deposited were obtained by filtering under reduced pressure. They were dried and then recrystallized from toluene to obtain 2-acetylfluorene (165 g) of colorless needle crystal. The melting point of this compound was 129° C.

Workup

  1. additioncontaining ice
  2. customthe solid matters deposited were obtained
  3. filtrationby filtering under reduced pressure
  4. customThey were dried
  5. customrecrystallized from toluene

Sources & evidence

ORD record
ord-921722096a384495b6910630f649aa1e
Source dataset
uspto-grants-2004_11
Patent number
US06824709B2

Reaction notes

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