Acetic Anhydride → HCID 66741118, compound

HRID 2387647Notes

Reaction equation

HRID 2387647 reaction equation
C([C:4]1[CH:16]=[CH:15][C:14]2[C:13]3[C:8](=[CH:9]C=[CH:11][CH:12]=3)[CH2:7][C:6]=2[CH:5]=1)(=O)C.[OH2:17].O.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+].C([O:33][C:34](=[O:36])[CH3:35])(=O)C>C(O)(=O)C.O>[C:34]([C:35]1[C:9](=[O:17])[C:8]2[C:13](=[CH:12][CH:11]=1)[C:14]1[C:6](=[CH:5][CH:4]=[CH:16][CH:15]=1)[CH:7]=2)([OH:33])=[O:36]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 699082-AcetylfluoreneHCID 108005Sodium dichromate dihydrate

Product 1

HCID 66741118HCID 66741118, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

2-Acetylfluorene (25.5 g, 0.12 mole) was dissolved in glacial acetic acid (325 mL). Sodium dichromate dihydrate (345 g, 1.16 mole) and acetic anhydride (138.4 mL, 1.46 mole) were added to the solution. The temperature of the reaction solution was increased to 120° C. (with reflux apparatus). The reaction was allowed to proceed for 16 hours. The reaction solution was cooled and diluted with distilled water (1.8 L). The solution was heated to approximately 80° C. and filtered. The precipitate was dissolved in 1M sodium hydroxide. The solution was washed with dichloromethane (3×160 mL). The aqueous solution was heated to approximately 80° C. and acidified with concentrated hydrochloric acid (pH approximately 2). The material was filtered and placed under vacuum to dry with phosphorus pentoxide present. The NMR spectrum was consistent with the loss of the acetyl methyl singlet and retention of other characteristic peaks.

Workup

  1. temperature(with reflux apparatus)
  2. temperatureThe reaction solution was cooled
  3. temperatureThe solution was heated to approximately 80° C.
  4. filtrationfiltered
  5. dissolutionThe precipitate was dissolved in 1M sodium hydroxide
  6. washThe solution was washed with dichloromethane (3×160 mL)
  7. temperatureThe aqueous solution was heated to approximately 80° C.
  8. filtrationThe material was filtered
  9. dry with materialto dry with phosphorus pentoxide present

Sources & evidence

ORD record
ord-81aedb863f8a41e096a57cf82b9bde5f
Source dataset
uspto-grants-2012_09
Patent number
US08268948B2

Reaction notes

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