Sulfuric Acid → 3-(4'-Methoxybenzoyl)benzofuran

HRID 1283649Notes

Reaction equation

HRID 1283649 reaction equation
[Mg].I[C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=1.[C:11]([C:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[O:15][CH:14]=1)#N.S(=O)(=O)(O)[OH:23]>O.CCOCC>[CH3:10][O:9][C:6]1[CH:7]=[CH:8][C:3]([C:11]([C:13]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[O:15][CH:14]=2)=[O:23])=[CH:4][CH:5]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 696764-IodoanisoleHCID 5462224MagnesiumHCID 157430851-Benzofuran-3-carbonitrile

Product 1

HCID 214879623-(4'-Methoxybenzoyl)benzofuran

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of the Grignard reagent prepared from 4.27 g. (0.14 g.-atom) of magnesium turnings and 31.0 g. (0.13 mol.) of 4-iodoanisole in 50 ml. of ether was added dropwise a solution of 10.0 g. (0.07 mol.) of 3-cyanobenzofuran in 150 ml. of ether. The reaction mixture was stirred at 25° for 17 hours, then 30 ml. of water was added followed by a mixture of 20 ml. of sulfuric acid and 40 ml. of water. Additional amounts of the acid solution were added to dissolve the precipitate that formed in the reaction mixture. The mixture was poured into 500 ml. of water and the aqueous solution was extracted with chloroform. The extracts were dried (MgSO4) and concentrated in vacuo to give 3-(4'-methoxybenzoyl)benzofuran which was purified by chromatography on alumina with chloroform, m.p. 89°-90° (hexane-benzene).

Workup

  1. additionfollowed by a mixture of 20 ml
  2. additionAdditional amounts of the acid solution were added
  3. dissolutionto dissolve the precipitate
  4. customthat formed in the reaction mixture
  5. additionThe mixture was poured into 500 ml
  6. extractionof water and the aqueous solution was extracted with chloroform
  7. dry with materialThe extracts were dried (MgSO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-65da100519974144857b5f9f91bfdb69
Source dataset
uspto-grants-1976_08
Patent number
US03975537

Reaction notes

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