Phosphorus oxychloride → 5-(Hexadecyloxy)thiophene-2-carbaldehyde

HRID 596632Notes

Reaction equation

HRID 596632 reaction equation
CN([CH:9]=[O:10])C1C=CC=CC=1.P(Cl)(Cl)(Cl)=O.[CH2:16]([O:32][C:33]1[S:34][CH:35]=[CH:36][CH:37]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]>>[CH2:16]([O:32][C:33]1[S:34][C:35]([CH:9]=[O:10])=[CH:36][CH:37]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 66737N-MethylformanilideHCID 214418272-(Hexadecyloxy)thiophene

Product 1

HCID 214418235-(Hexadecyloxy)thiophene-2-carbaldehyde

Conditions

Temperature
70 °C

Procedure

To a cooled mixture of 27 g of N-methylformanilide in 27 g (0.176 mole) of phosphorusoxy chloride is added 32.5 g (0.1 mole) of 2-hexadecyloxythiophene. The mixture is warmed to 70° C under vacuum (10 mm Hg). The mixture is allowed to stand at 60° to 70° 20 C for 7 hours, then overnight at room temperature after which the mixture is stirred into 100 g of ice. The mixture is extracted into benzene, washed with water, dried over sodium sulfate and distilled in vacuo to give 5-hexadecyloxy-2-thiophenecarboxaldehyde.

Workup

  1. customto stand at 60° to 70°
  2. customfor 7 hours
  3. extractionThe mixture is extracted into benzene
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. distillationdistilled in vacuo

Sources & evidence

ORD record
ord-e88de968da5e4c80806742899b9f431f
Source dataset
uspto-grants-1977_03
Patent number
US04011334

Reaction notes

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