Benzaldehyde → HCID 13798876, compound

HRID 1721991Notes

Reaction equation

HRID 1721991 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][NH:6][CH2:7][CH:8]([OH:11])[CH2:9][OH:10])[CH3:2].[CH:12](=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(O)(=O)C1C=CC=CC=1.C1(C)C=CC=CC=1>[C:13]1([CH:12]2[N:6]([CH2:5][CH2:4][O:3][CH2:1][CH3:2])[CH2:7][CH:8]([CH2:9][OH:10])[O:11]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 240BenzaldehydeHCID 13798875HCID 13798875, compound

Product 1

HCID 13798876HCID 13798876, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 243Benzoic AcidCatalystHCID 1140TolueneSolvent

Procedure

A solution of 1 (22.6 g, 0.14 mol), toluene (120 ml), benzaldehyde (48 g, 0.45 mol) and benzoic acid (0.5 g) was heated at reflux with a Dean-Stark trap. After 1.5 hours, the theoretical amount of H2O was collected, the reaction mixture was cooled to room temperature and added to saturated Na2CO3. The aqueous layer was separated and washed with CHCl3 (3X). The combined extracts were dried, filtered, and concentrated to dryness. The residue was distilled at 145°-50° C. at 0.4 mm to yield 26 g (75%) of 2.

Workup

  1. temperatureat reflux with a Dean-Stark trap
  2. customthe theoretical amount of H2O was collected
  3. additionadded to saturated Na2CO3
  4. customThe aqueous layer was separated
  5. washwashed with CHCl3 (3X)
  6. customThe combined extracts were dried
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. distillationThe residue was distilled at 145°-50° C. at 0.4 mm

Sources & evidence

ORD record
ord-bcd8a85725744f3688f8d58916b50fa8
Source dataset
uspto-grants-1989_08
Patent number
US04853383

Reaction notes

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