Sodium Hydroxide → p-Dodecyloxybenzaldehyde

HRID 1760899Notes

Reaction equation

HRID 1760899 reaction equation
[CH2:1]([O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].CN([CH:28]=[O:29])C1C=CC=CC=1.O=P(Cl)(Cl)Cl.[OH-].[Na+]>>[CH2:1]([O:13][C:14]1[CH:15]=[CH:16][C:17]([CH:28]=[O:29])=[CH:18][CH:19]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 4

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 66737N-MethylformanilideHCID 294549Ether, dodecyl phenyl

Product 1

HCID 141069p-Dodecyloxybenzaldehyde

Procedure

Dodecyloxybenzene (2.48 g; 9.45 mmol) is dissolved in N-methylformanilide (195.17 g; 9.45 mmol). POCl3 (1.45 g; 159.33 g; 9.45 mmol) is added dropwise with ice-cooling. Stirring is carried out for 1 hour at 25° C., and then for 3 hours at 60° C. Pouring onto ice is then carried out and the pH is adjusted to 6 using sodium hydroxide solution. Extraction is then carried out with tert-butyl methyl ether (2×50 ml), and the combined organic phases are washed with aqueous NaHCO3 solution and dried over Na2SO4. After filtration, concentration to dryness by evaporation is carried out.

Workup

  1. temperaturecooling
  2. waitfor 3 hours at 60° C
  3. additionPouring onto ice
  4. extractionExtraction
  5. washthe combined organic phases are washed with aqueous NaHCO3 solution
  6. dry with materialdried over Na2SO4
  7. filtrationAfter filtration, concentration to dryness
  8. customby evaporation

Sources & evidence

ORD record
ord-9af5880bf14344bc89e9c4d3fd366fa5
Source dataset
uspto-grants-2005_01
Patent number
US06846492B2

Reaction notes

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