Benzaldehyde → HCID 10987985, compound

HRID 1834413Notes

Reaction equation

HRID 1834413 reaction equation
I.[PH2](O)=O.[CH3:5][C:6]1[NH:7][CH:8]=[C:9]([CH3:14])[C:10]=1[C:11](=[O:13])[CH3:12].[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(OC(=O)C)(=O)C.O>[CH3:5][C:6]1[NH:7][C:8]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:9]([CH3:14])[C:10]=1[C:11](=[O:13])[CH3:12]

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 15163Ketone, 2,4-dimethylpyrrol-3-yl methylHCID 24841Hydrogen iodideHCID 4124402Phosphinic Acid

Product 1

HCID 10987985HCID 10987985, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7918Acetic AnhydrideSolvent2×

Procedure

A solution of 10 ml of aqueous hydriodic acid, 10 ml of acetic anhydride and 2 ml of 50% hypophosphorous acid containing 548 mg of 2,4-dimethyl-3acetyl pyrrole was stirred magnetically while a solution of 0.6 ml of benzaldehyde in 5 ml of acetic anhydride was slowly added over 20 mins. The solution was stirred for 10 mins, then poured into water. The crude product which separated was recrystallized from acetone (thimble) as nearly colourless irregular plates (85%, m.p. 165.5°-167° C. after a partial change to prismatic rods above 165° C. Anal. Cal. for C15H17NO: C, 79.26; H, 7.54; N, 6.16. Found: C, 79.22; H, 7.50; N, 6.18.

Workup

  1. additionwas slowly added over 20 mins
  2. customThe crude product which separated
  3. customwas recrystallized from acetone (thimble) as nearly colourless irregular plates (85%, m.p. 165.5°-167° C. after a partial change to prismatic rods above 165° C

Sources & evidence

ORD record
ord-07403b26b50e48a1aa0376b113c057e5
Source dataset
uspto-grants-1978_01
Patent number
US04070366

Reaction notes

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