Salicylaldehyde → 3-(4-Methoxybenzoyl)-2H-1-benzopyran-2-one

HRID 1526119Notes

Reaction equation

HRID 1526119 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:16])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5][CH:4]=1.N1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.OC1C=CC=CC=1C=O>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]([C:10]2[C:11](=[O:12])[O:13][C:14]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][CH:15]=3)=[O:16])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 6998SalicylaldehydeHCID 8082PiperidineHCID 76150Benzenepropanoic acid, 4-methoxy-beta-oxo-, ethyl ester

Product 1

HCID 127770683-(4-Methoxybenzoyl)-2H-1-benzopyran-2-oneYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.64 g (16.38 mmol) of ethyl 3-(4-methoxyphenyl)-3-oxopropanoate and 1.39 g of piperidine (16.38 mmol) are added to a solution of 2 g (16.38 mmol) of 2-hydroxybenzaldehyde in 15 ml of ethanol. The reaction mixture is stirred for 8 hours at reflux. The solution is cooled, and then the white solid formed is filtered and rinsed with a minimum of ethanol to yield 4.02 g (88%) of 3-(4-methoxybenzoyl)-2H-chromen-2-one.

Workup

  1. temperatureat reflux
  2. temperatureThe solution is cooled
  3. customthe white solid formed
  4. filtrationis filtered
  5. washrinsed with a minimum of ethanol

Sources & evidence

ORD record
ord-1a71fefa8be645ff8e11e47c44215b55
Source dataset
uspto-grants-2015_07
Patent number
US09085575B2

Reaction notes

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