Phosphorus oxychloride → 3,4-dihexyloxybenzaldehyde

HRID 1760902Notes

Reaction equation

HRID 1760902 reaction equation
[CH2:1]([O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].CN([CH:29]=[O:30])C1C=CC=CC=1.P(Cl)(Cl)(Cl)=O>>[CH2:15]([O:14][C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][C:8]=1[O:7][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH:29]=[O:30])[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 66737N-MethylformanilideHCID 43816021,2-Dihexyloxybenzene

Product 1

HCID 118229373,4-dihexyloxybenzaldehyde

Conditions

Temperature
60 °C

Procedure

1,2-Dihexyloxybenzene (11.14 g; 40 mmol) and N-methylformanilide (5.41 g; 40 mmol) are cooled to 0° C., and phosphorus oxychloride (6.13 g; 40 mmol) is added. Heating is then carried out for 1 hour at 25° C., followed by stirring for 4 hours at 60° C. The reaction mixture is poured onto ice and then adjusted to pH 6. Extraction is carried out with tert-butyl methyl ether (2×200 ml), and washing is carried out with NaHCO3 (2×100 ml). The organic phase is dried over Na2SO4, filtered and concentrated to dryness by evaporation.

Workup

  1. temperatureHeating
  2. additionThe reaction mixture is poured onto ice
  3. extractionExtraction
  4. washwashing
  5. dry with materialThe organic phase is dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness by evaporation

Sources & evidence

ORD record
ord-187fa965f2434963ab1d1967127ec126
Source dataset
uspto-grants-2005_01
Patent number
US06846492B2

Reaction notes

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