Benzaldehyde → Hydrobenzamide

HRID 36003Notes

Reaction equation

HRID 36003 reaction equation
[NH4+:1].[OH-].[CH:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CC(O)C>[CH:7]1[CH:8]=[CH:9][C:4](/[CH:3]=[N:1]/[CH:3]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)/[N:1]=[CH:3]/[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 14923Ammonium Hydroxide

Product 1

HCID 9566477HydrobenzamideYield 97.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a 3 L 3-necked flask equipped with a mechanical stirrer and a thermometer was added 1 L of concentrated NH4OH (ca 30%) (14.8 moles). A solution of benzaldehyde (265 g, 2.50 mol) in 500 mL of 2-propanol was added in one portion. The mixture was stirred vigorously at ca 22° C. for 43 hr. The resulting slurry was filtered and the filter cake was washed with water (1 L). After drying in vacuo, 242.4 g of hydrobenzamide was obtained as a white solid (mp 100°-102° C.) for a 97.4% yield.

Workup

  1. customTo a 3 L 3-necked flask equipped with a mechanical stirrer
  2. filtrationThe resulting slurry was filtered
  3. washthe filter cake was washed with water (1 L)
  4. customAfter drying in vacuo

Sources & evidence

ORD record
ord-1782baef276b43558edf525bcf776e68
Source dataset
uspto-grants-1995_05
Patent number
US05412092

Reaction notes

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