HCID 21071774, compound → HCID 21071791, compound

HRID 1372161Notes

Reaction equation

HRID 1372161 reaction equation
CO[CH:3](OC)[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([I:12])=[CH:8][C:7]=1[CH3:13]>ClC1C=CC=CC=1>[I:12][C:9]1[CH:8]=[C:7]([CH3:13])[C:6]2[O:5][CH:4]=[CH:3][C:11]=2[CH:10]=1

Participants

3

Reactant 1

HCID 21071774HCID 21071774, compound

Product 1

HCID 21071791HCID 21071791, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent2×

Procedure

To a 1 L 3-neck flask was added PPA (2.0 g), anhydrous chlorobenzene (300 ml) and the mixture was brought to reflux. Then 1-(2,2-dimethyoxy-ethoxy)-4-iodo-2-methyl benzene (11.16 g, 34.66 mmol) in chlorobenzene (80 ml) was slowly added by addition funnel over a 2 h period. The reaction was then cooled and passed through a silica plug (washed with chlorobenzene) and concentrated to a mixture of product plus 4-iodo-2-methylphenol. Column chromatography (100% hexane) afforded 4.49 g (53%) product as a clear oil: 1H NMR (300 MHz, DMSO-d6): δ 2.44 (3H, s), 6.91 (1H, d, J=2.2 Hz), 7.46 (1H, brs), 7.86 (1H, d, J=1.2 Hz), 8.00 (1H, d, J=2.2 Hz); MS (E) m/z 258 ([M]+).

Workup

  1. temperatureto reflux
  2. temperatureThe reaction was then cooled
  3. concentrationconcentrated to a mixture of product plus 4-iodo-2-methylphenol

Sources & evidence

ORD record
ord-15a36c23d0794627991ce2c693b06fc3
Source dataset
uspto-grants-2007_01
Patent number
US07157491B2

Reaction notes

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