Dibenzofuran → 2-Acetyldibenzofuran

HRID 1781174

Reaction equation

HRID 1781174 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH:5]1[C:13]2[C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[O:10][C:9]=2[CH:8]=[CH:7][CH:6]=1.[C:18](Cl)(=[O:20])[CH3:19]>ClC(Cl)C>[C:18]([C:6]1[CH:7]=[CH:8][C:9]2[O:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[C:13]=2[CH:5]=1)(=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 568DibenzofuranHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 2930282-AcetyldibenzofuranYield 28.3%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Aluminum chloride (23.8 g, 178.4 mmol) was added portionwise to a solution of dibenzofuran (30.0 g, 178.4 mmol) and acetyl chloride (14.0 g, 178.4 mmol) in dichloroethane at 0° C. After 8 hours, the reaction was quenched with 6N HCl. The layers were separated and the methylene chloride layer was dried (MgSO4), filtered and concentrated to provide a yellow solid. The solid was recrystallized 3 times from hexane to provide 10.6 g (28%) of the title compound as a white solid. 1H NMR (CDCl3, 300 MHz) δ 2.7 (s, 3H), 7.4 (dt, J=7.5 Hz, 0.5 Hz, 1H), 7.5 (dt, J=7.5 Hz, 0.5 Hz, 1H), 7.65 (d, J=7.5 Hz, 2H), 8.0 (d, J=7.5 Hz, 1H), 8.15 (dd, J=7.5 Hz, 0.5 Hz), 8.6 (d, J=0.5 Hz). MS (DCl/NH3) m/e 211 (M+H)+.

Workup

  1. customthe reaction was quenched with 6N HCl
  2. customThe layers were separated
  3. dry with materialthe methylene chloride layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto provide a yellow solid
  7. customThe solid was recrystallized 3 times from hexane

Sources & evidence

ORD record
ord-b2b29368f8524ef8a54a46dbbda5d4cb
Source dataset
uspto-grants-1997_05
Patent number
US05631401

Linked notes

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