Water → 2-Acetylfluorenon

HRID 328243Notes

Reaction equation

HRID 328243 reaction equation
[C:1]([C:4]1[CH:16]=[CH:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:7][C:6]=2[CH:5]=1)(=[O:3])[CH3:2].[O-:17][Cr](O[Cr]([O-])(=O)=O)(=O)=O.[Na+].[Na+].O.[OH-].[Na+]>C(O)(=O)C>[C:1]([C:4]1[C:5](=[O:17])[C:6]2[C:14](=[CH:15][CH:16]=1)[C:13]1[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH:7]=2)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 25408Sodium DichromateHCID 699082-Acetylfluorene

Product 1

HCID 676152522-AcetylfluorenonYield 38%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 77.0 g (0.74 mol) of 2-acetylfluorene in 1.1 l of acetic acid are added at 90° C and under intense stirring, 385 g (1.3 mol) of sodium bichromate during a period of 1 hr to 1 hr 15 min. Thereupon, the reaction mixture is allowed to stand under the same conditions for 4 hours, then poured into 4.6 l of water heated to 90° C and kept overnight at room temperature. The precipitate is filtered off, washed with 900 ml of a 2-percent sulfuric acid till a colorless wash solution appears, and with water until the acid reaction disappears. Then the precipitate is treated under intense stirring, with 540 ml of a 5-percent caustic soda solution heated to 90° C, and let cool down to room temperature. The precipitate is filtered off, washed with water and dried in a drying cabinet at 80° C to obtain 62.5 g of crude 2-acetylfluorenone which is then recrystallized from 1.0 l of benzene for the sake of purity. The yield of 2-acetylfluorenone equals 55.5 g (68.0 wt% as calculated for 2-acetylfluorene or 50 wt.% when calculated for fluorene), m.p. 160°-161.5° C.

Workup

  1. waitkept overnight at room temperature
  2. filtrationThe precipitate is filtered off
  3. washwashed with 900 ml of a 2-percent sulfuric acid till a colorless wash solution
  4. customwith water until the acid reaction
  5. temperatureheated to 90° C
  6. temperaturelet cool down to room temperature
  7. filtrationThe precipitate is filtered off
  8. washwashed with water
  9. customdried in a drying cabinet at 80° C

Sources & evidence

ORD record
ord-800ad97d76ee4e268c01836a5a7c5d87
Source dataset
uspto-grants-1977_04
Patent number
US04016289

Reaction notes

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