3-(2,2-Dimethoxy-ethoxy)-4'-methoxy-4-methyl-biphenyl → 4-(4-Methoxyphenyl)-7-methylbenzofuran

HRID 1372158Notes

Reaction equation

HRID 1372158 reaction equation
CO[CH:3](OC)[CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[CH:9]=[CH:10][C:11]=1[CH3:12]>ClC1C=CC=CC=1>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([C:8]2[C:7]3[CH:3]=[CH:4][O:5][C:6]=3[C:11]([CH3:12])=[CH:10][CH:9]=2)=[CH:14][CH:15]=1

Participants

3

Reactant 1

HCID 210717783-(2,2-Dimethoxy-ethoxy)-4'-methoxy-4-methyl-biphenyl

Product 1

HCID 210717824-(4-Methoxyphenyl)-7-methylbenzofuran

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent2×

Procedure

A mixture of polyphosphoric acid (approx. 0.5 g) and chlorobenzene was brought to reflux and 3-(2,2-dimethoxy-ethoxy)-4′-methoxy-4-methyl-biphenyl (1.61 g, 5.33 mmol) in chlorobenzene (12 ml) was added dropwise. After 4 h the reaction was cooled, passed through a silica plug (the plug was washed with ether), and concentrated to 1.26 g (100%) of product as a light tan solid: mp 40–41° C.; 1H NMR (300 MHz, DMSO-d6): δ 2.50 (3H, s), 3.82 (3H, s), 7.03 (1H, d, J=2.2 Hz), 7.07 (2H, d, J=9.5 Hz), 7.19 (1H, d, J=8.1 Hz), 7.23 (1H, d, J=8.1 Hz), 7.56 (2H, d, J=9.5 Hz), 8.06 (1H, d, J=2.2 Hz).

Workup

  1. temperatureto reflux
  2. temperatureAfter 4 h the reaction was cooled
  3. washwas washed with ether), and
  4. concentrationconcentrated to 1.26 g (100%) of product as a light tan solid

Sources & evidence

ORD record
ord-f81764715e4246969f90d14f38bfb8dd
Source dataset
uspto-grants-2007_01
Patent number
US07157491B2

Reaction notes

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