Butanal → HCID 21427377, compound

HRID 438024Notes

Reaction equation

HRID 438024 reaction equation
[P:1]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[O:2]C1C=CC=CC=1.[CH:23](=O)[CH2:24][CH2:25][CH3:26].[CH3:28][C:29]1[CH:30]=[CH:31][C:32]([S:35]([NH2:38])(=[O:37])=[O:36])=[CH:33][CH:34]=1>ClC1C=CC=CC=1>[C:29]1([CH3:28])[CH:30]=[CH:31][C:32]([S:35]([NH:38][CH:23]([P:1](=[O:2])([O:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[O:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:24][CH2:25][CH3:26])(=[O:37])=[O:36])=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 261ButanalHCID 6269P-ToluenesulfonamideHCID 7540Triphenyl phosphite

Product 1

HCID 21427377HCID 21427377, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A mixture of 0.5 mole each of triphenyl phosphite, n-butyraldehyde and p-toluenesulfonamide in 150 g of chlorobenzene is stirred and warmed under nitrogen. An exothermic reaction is detectable at 85° C., and cooling is used for a few minutes to keep the temperature below 93°. Heating is then continued at 95°-100° for 0.75 hr to ensure complete reaction. The reaction mixture is cooled to 25° and filtered. The product is recrystallized from acetonitrile, giving 202 g (88% yield) of white solid: mp 178°-180°; 31P nmr(DMSO-d6)- 17.7 ppm.

Workup

  1. temperaturewarmed under nitrogen
  2. customAn exothermic reaction
  3. customis detectable at 85° C.
  4. temperaturecooling
  5. waitis used for a few minutes
  6. customthe temperature below 93°
  7. temperatureHeating
  8. customreaction
  9. temperatureThe reaction mixture is cooled to 25°
  10. filtrationfiltered
  11. customThe product is recrystallized from acetonitrile

Sources & evidence

ORD record
ord-c0ae2d13443943998a123be9f2db8eb1
Source dataset
uspto-grants-1977_06
Patent number
US04032601

Reaction notes

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