Hydrochloric Acid → 2-Acetyl-7-octylfluorene

HRID 249214Notes

Reaction equation

[CH2:1]([C:9]1[CH:21]=[CH:20][C:19]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][C:11]=2[CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[Cl-].[Al+3].[Cl-].[Cl-].[C:26](Cl)(=[O:28])[CH3:27].Cl>C(=S)=S>[C:26]([C:15]1[CH:16]=[CH:17][C:18]2[C:19]3[C:11](=[CH:10][C:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:21][CH:20]=3)[CH2:12][C:13]=2[CH:14]=1)(=[O:28])[CH3:27]

Participants

Conditions

Temperature: -20 °C

Procedure

To a solution of 4.50 g (16.2 mM) of 2-octylfluorene in 50 ml of dry carbon disulfide, 2.70 g (20.2 mM) of pulverized anhydrous aluminum chloride was added while being cooled on an ice-common salt bath. Under cooling on the bath, 1.20 ml (16.9 mM) of acetyl chloride was added dropwise to the mixture below 7° C., followed by stirring for 1 hour and 50 minutes at 10° C. or below. 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 condensed, followed by cooling to about -20° C. to precipitate a crystal. The crystal was recovered by filtration to obtain 3.97 g of 2-acetyl-7-octylfluorene (Yield: 76.6%).

Workup

temperaturewhile being cooled on an ice-common salt bath
additionwas added dropwise to the mixture below 7° C.
customAfter the reaction
extractionfollowed by extraction with ethyl acetate
washThe organic layer was washed with water
dry with materialdried with anhydrous sodium sulfate, and condensed
customto precipitate a crystal
filtrationThe crystal was recovered by filtration

Sources & evidence

ORD record: ord-f766b1bbf6364a369213d885ee18d0c2
Source dataset: uspto-grants-1993_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05213709

Reaction notes

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