Perylene → 3-Perylenecarboxaldehyde

HRID 267469

Reaction equation

HRID 267469 reaction equation
CN([CH:9]=[O:10])C1C=CC=CC=1.P(Cl)(Cl)(Cl)=O.[CH:16]1[C:33]2=[C:34]3[C:23]([C:24]4[C:35]5[C:28](=[CH:29][CH:30]=[CH:31][C:32]2=5)[CH:27]=[CH:26][CH:25]=4)=[CH:22][CH:21]=[CH:20][C:19]3=[CH:18][CH:17]=1.C([O-])(=O)C.[Na+]>ClC1C=CC=CC=1Cl.O>[CH:31]1[C:32]2=[C:35]3[C:24]([C:23]4[C:34]5[C:19](=[CH:18][CH:17]=[CH:16][C:33]2=5)[CH:20]=[CH:21][CH:22]=4)=[CH:25][CH:26]=[CH:27][C:28]3=[C:29]([CH:9]=[O:10])[CH:30]=1

Participants

7

Reactant 4

HCID 9142PeryleneHCID 24813Phosphorus oxychlorideHCID 66737N-MethylformanilideHCID 517045Sodium Acetate

Product 1

HCID 36989163-Perylenecarboxaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 72391,2-DichlorobenzeneSolvent

Procedure

About 22 grams N-methylformanilide is initially dissolved in 40 milliliters o-dichlorobenzene, the vessel containing the above solution partially immersed in a water bath (bath temperature less than 25° C) and 22 grams phosphorous oxychloride introduced into the flask by dropewise addition. About 20 grams of perylene is stirred into the above solution and the resulting mixture heated on a steam bath for twelve hours (temperature of contents of vessel 90°-95° C). The contents of the flask are thereafter poured into a second vessel containing 100 grams sodium acetate dissolved in 250 milliliters water. The organic liquid phase of the mixture is separated from the aqueous phase by steam distillation. Crude aldehyde is thereafter precipitated from aqueous solution and the solids recystalized from acetic acid and from benzene. The solids thus obtained are further extracted in a soxhlet extractor with 30-60 pet ether. The material remaining in the extraction thimble is 3-perylenecarboxaldehyde, mp 230° C; yield 9.5 grams.

Workup

  1. additionthe vessel containing the above solution
  2. custompartially immersed in a water bath
  3. temperaturethe resulting mixture heated on a steam bath for twelve hours (temperature of contents of vessel 90°-95° C)
  4. additionThe contents of the flask are thereafter poured into a second vessel
  5. customThe organic liquid phase of the mixture is separated from the aqueous phase by steam distillation
  6. customCrude aldehyde is thereafter precipitated from aqueous solution
  7. customThe solids thus obtained
  8. extractionare further extracted in a soxhlet extractor with 30-60 pet ether

Sources & evidence

ORD record
ord-208a3fab508844b2a70188954870e1fd
Source dataset
uspto-grants-1976_03
Patent number
US03943108

Linked notes

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