p-Toluenesulfonic acid monohydrate → HCID 19047538, compound

HRID 742451Notes

Reaction equation

HRID 742451 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH:10]1[C:15]2[CH:16]=[CH:17][O:18][C:14]=2[CH:13](O)[CH2:12][CH2:11]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[C:15]2[CH:16]=[CH:17][O:18][C:14]=2[CH2:13][CH2:12][CH:11]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 19047457HCID 19047457, compound

Product 1

HCID 19047538HCID 19047538, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 19.3 g of 4,5,6,7-tetrahydro-4-(2-benzofuryl)-benzofuran-7-ol in 400 mL of toluene was added 100 mg of p-toluenesulfonic acid monohydrate, and the mixture was placed on a Rotovap, and the solvent was distilled in vacuo (60° C.) until a residue was obtained. The residue was chromatographed on silica (hexane/methylene chloride 1.5:1) to afford 15.3 g (86%) of 6,7-dihydro-4-(2-benzofuryl)-benzofuran, (Formula Ill: R3 =H; ##STR53## R5 =2-benzofuryl) as an orange oil.

Workup

  1. distillationthe solvent was distilled in vacuo (60° C.) until a residue
  2. customwas obtained
  3. customThe residue was chromatographed on silica (hexane/methylene chloride 1.5:1)

Sources & evidence

ORD record
ord-3dbb31087358432f90afd5f34479d842
Source dataset
uspto-grants-1996_09
Patent number
US05554620

Reaction notes

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