HCID 59595831, compound → 5-Phenyl-1-benzofuran

HRID 2264536Notes

Reaction equation

HRID 2264536 reaction equation
C(O[CH:4](OCC)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)C>C1C=CC=CC=1>[C:13]1([C:10]2[CH:9]=[CH:8][C:7]3[O:6][CH:5]=[CH:4][C:12]=3[CH:11]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

3

Reactant 1

HCID 59595831HCID 59595831, compound

Product 1

HCID 142489325-Phenyl-1-benzofuranYield 83.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 1-(2,2-diethoxyethoxy)-4-phenylbenzene (3.52 g, 12.3 mmol) and polyphosphoric acid (2.95 g, 29.4 mmol) in benzene (60 mL) was stirred at reflux for 2 h. The reaction mixture was cooled to room temperature, decanted from the PPA and filtered through a plug of silica gel, which was washed with hexanes. The filtrate and the wash were combined and concentrated under reduced pressure to yield 2.00 g of the crude benzofuran: 1H NMR (400 MHz, CD3OD) δ 7.79 (dd, 1H), 7.66 (d, 1H), 7.63-7.60 (m, 2H), 7.58-7.51 (m, 2H), 7.45 (t, 2H), 7.36-7.33 (m, 1H), 6.82 (dd, 1H).

Workup

  1. temperatureat reflux for 2 h
  2. customdecanted from the PPA
  3. filtrationfiltered through a plug of silica gel, which
  4. washwas washed with hexanes
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-17687d2cf51d402fb445324631d617fa
Source dataset
uspto-grants-2010_12
Patent number
US07855193B2

Reaction notes

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