Methanol → 2-Chloro-9H-fluoren-9-one

HRID 1073327Notes

Reaction equation

HRID 1073327 reaction equation
C[OH:2].[Cl:3][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>N1C=CC=CC=1.O=O>[Cl:3][C:4]1[CH:16]=[CH:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:2])[C:6]=2[CH:5]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 17300Fluorene, 2-chloro- (8CI)

Product 1

HCID 183542-Chloro-9H-fluoren-9-one

Reagents, catalysts & solvents 2

HCID 977OxygenSolventHCID 1049PyridineSolvent2×

Procedure

A methanol free, 40% solution of Triton B in pyridine (8 mL) was added to a stirred, room temperature solution of commercially available (Alpha) 2-chlorofluorene (17) (42 g, 0.21 mmoL) in pyridine (257 mL) and oxygen was bubbled through the mixture at a moderate rate for 18 h. The majority of the pyridine was then removed on the rotary evaporator at reduced pressure and 5% aqueous hydrochloric acid (500 mL) was added to the residue. The solid was collected by filtration and washed with 5% aqueous hydrochloric acid and water. After drying, the solid was extracted repeatedly with hexane to remove some hexane insoluble impurities. Evaporation of the hexane left 42.7 g(95%) of 2-chloro-9-fluorenone: mp 110°-113° C.

Workup

  1. customwas bubbled through the mixture at a moderate rate for 18 h
  2. customThe majority of the pyridine was then removed on the rotary evaporator at reduced pressure and 5% aqueous hydrochloric acid (500 mL)
  3. additionwas added to the residue
  4. filtrationThe solid was collected by filtration
  5. washwashed with 5% aqueous hydrochloric acid and water
  6. customAfter drying
  7. extractionthe solid was extracted repeatedly with hexane
  8. customto remove some hexane insoluble impurities
  9. customEvaporation of the hexane
  10. waitleft 42.7 g(95%) of 2-chloro-9-fluorenone

Sources & evidence

ORD record
ord-44f891b38d054409b7efee64624e56fc
Source dataset
uspto-grants-1990_11
Patent number
US04968809

Reaction notes

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