Hydrochloric Acid → 3-Formyl-2-methyl-7-nitrobenzo[b]furan

HRID 342423

Reaction equation

HRID 342423 reaction equation
[CH3:1][C:2]1[O:6][C:5]2[C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=[CH:10][C:4]=2[CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[CH3:18][O:19]C(Cl)Cl.Cl>ClCCl>[CH:18]([C:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:5]=2[O:6][C:2]=1[CH3:1])=[O:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 21004Methane, dichloromethoxy-HCID 6451240Aluminum(III) ChlorideHCID 132018972-Methyl-7-nitrobenzofuran

Product 1

HCID 867535523-Formyl-2-methyl-7-nitrobenzo[b]furan

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 2-methyl-7-nitrobenzo[b]furan (1.77 g) and aluminum chloride (2.66 g) in dichloromethane (40 ml) was added dropwise a solution of dichloromethyl methyl ether (3.6 ml) in dichloromethane (10 ml). The mixture was stirred at ambient temperature for 30 minutes and the reaction mixture was poured into a mixture of ice and 1N-hydrochloric acid. The separated oil was extracted with dichloromethane and the extract was washed with brine, aqueous saturated sodium bicarbonate and brine. Then, the solution was dried over sodium sulfate and evaporated in vacuo. The obtained oil was crystallized from diethyl ether to give 3-formyl-2-methyl-7-nitrobenzo[b]furan (1.83 g).

Workup

  1. extractionThe separated oil was extracted with dichloromethane
  2. washthe extract was washed with brine, aqueous saturated sodium bicarbonate and brine
  3. dry with materialThen, the solution was dried over sodium sulfate
  4. customevaporated in vacuo
  5. customThe obtained oil was crystallized from diethyl ether

Sources & evidence

ORD record
ord-02a255bdb6784c9caf126c55bafac015
Source dataset
uspto-grants-1999_01
Patent number
US05858995

Linked notes

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