Dichloromethane → HCID 12327003, compound

HRID 1287933Notes

Reaction equation

HRID 1287933 reaction equation
C(Cl)(=O)[C:2](Cl)=[O:3].[CH3:7][O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([C:19]2[O:20][C:21]3[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=3[CH:23]=2)=[CH:11][CH:10]=1.C(Cl)Cl>O>[CH3:7][O:8][C:9]1[CH:10]=[CH:11][C:12]2=[C:13]3[C:18]=1[CH:17]=[CH:16][CH:15]=[C:14]3[C:2](=[O:3])[C:23]1[C:22]3[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=3[O:20][C:19]=12

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 123269992-(4-Methoxynaphthalen-1-yl)-1-benzofuran

Product 1

HCID 12327003HCID 12327003, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Alternatively, 3-methoxy-7-oxo-7H-benzo[b]-phenaleno[2,1-d]furan was prepared by addition of 0.38 ml. (45 mmol.) of oxalyl chloride followed by 1.2 ml. (0.01 mol.) of stannic chloride to a solution of 1 g. (37 mmol.) of 2-(4-methoxynaphthyl)benzofuran in 100 ml. of methylene chloride at 0°. The reaction mixture was stirred for 1.5 hours at 0° then poured into water. The layers were separated and the organic phase was washed with 10% aqueous sodium carbonate, dried (MgSO4) and evaporated to dryness. The residue was chromatographed on silica with chloroform as eluant to give the product.

Workup

  1. customat 0°
  2. customThe layers were separated
  3. washthe organic phase was washed with 10% aqueous sodium carbonate
  4. dry with materialdried (MgSO4)
  5. customevaporated to dryness
  6. customThe residue was chromatographed on silica with chloroform as eluant
  7. customto give the product

Sources & evidence

ORD record
ord-54bcbfa08a054062b4a9ce90bf79f2b9
Source dataset
uspto-grants-1976_10
Patent number
US03985896

Reaction notes

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