Benzaldehyde → HCID 20221015, compound

HRID 980840Notes

Reaction equation

HRID 980840 reaction equation
[CH3:1][C:2]1[N:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6]CC)=[O:5].[CH:13](=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(OC(=O)C)(=O)C>>[OH:20][CH:13]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:1][C:2]1[N:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 3

HCID 240BenzaldehydeHCID 7918Acetic AnhydrideHCID 74401Ethyl 2-methylnicotinate

Product 1

HCID 20221015HCID 20221015, compound

Procedure

In carrying out the reaction, an appropriate ethyl 2-methylnicotinate and benzaldehyde compound and acetic anhydride are refluxed together under nitrogen for about 24 hours. Thereafter, the excess anhydride is removed in vacuo and the residue poured into water and extracted with ether. The ether solution extracted with dilute acid, the acid solution then made basic with ammonia to obtain a lactone of 2-(2-hydroxy-2-phenylethyl)nicotinic acid. The lactone is reduced to 2-phenylethylnicotinic acid adding the lactone to a freshly prepared mixture of phosphorus and iodine and the resulting mixture heated at reflux temperature for 3 to 10 hours with stirring. The acid is recovered from the reaction mixture by filtering to remove the phosphorus and cooling to recover the hydroiodic acid salt which is collected, dissolved in water and the solution neutralized with ammonia to obtain the 2-phenethylnicotinic acid.

Workup

  1. customthe reaction
  2. customThereafter, the excess anhydride is removed in vacuo
  3. additionthe residue poured into water
  4. extractionextracted with ether
  5. extractionThe ether solution extracted
  6. additionwith dilute acid

Sources & evidence

ORD record
ord-8ba91680310444f68af706c84a9f4aa7
Source dataset
uspto-grants-1987_01
Patent number
US04639457

Reaction notes

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