Benzaldehyde → HCID 254083, compound

HRID 2284377Notes

Reaction equation

HRID 2284377 reaction equation
[CH2:1]1[C:6](=[O:7])[O:5][CH2:4][C:2]1=[O:3].[CH:8](=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl>CCCCCC>[CH:8](=[C:1]1[C:2](=[O:3])[CH2:4][O:5][C:6]1=[O:7])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 521261Tetronic acid

Product 1

HCID 254083HCID 254083, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Tetronic acid (300 mg, 3 mmol) was added to benzaldehyde (1.0 mL, 9 mmol), and the resulting solution was stirred. HCl (37.7%, 0.1 mL) was added drop wise. The reaction mixture was vigorously stirred until it solidified. The solid product was crushed, soaked in hexane and washed with hexane. The crude product was purified by recrystallization (ethyl acetate/hexanes=8/2) to give compound TC-I-49 (0.27 g, 48%) as a yellow solid.

Workup

  1. stirringThe reaction mixture was vigorously stirred until it
  2. customThe solid product was crushed
  3. washwashed with hexane
  4. customThe crude product was purified by recrystallization (ethyl acetate/hexanes=8/2)
  5. customto give compound TC-I-49 (0.27 g, 48%) as a yellow solid

Sources & evidence

ORD record
ord-e5d0773169284012a3b9261c47e54058
Source dataset
uspto-grants-2015_09
Patent number
US09145424B2

Reaction notes

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