Benzaldehyde → 4-Hydroxy-3-benzylcoumarin

HRID 983502Notes

Reaction equation

HRID 983502 reaction equation
C([O-])=O.C([NH+](CC)CC)C.C(O)=O.[CH:14](=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O[C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[O:26][C:25](=[O:33])[CH:24]=1>O>[CH2:23]([C:24]1[C:25](=[O:26])[O:33][C:20]2[C:15]([C:14]=1[OH:21])=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:32]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 284Formic AcidHCID 10219518Triethylazanium;formate2×HCID 546829304-Hydroxycoumarin

Product 1

HCID 546861124-Hydroxy-3-benzylcoumarin

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
135 °C

Procedure

Triethylammonium formate (TEAF) was prepared by adding TEA (20.0 mL) to formic acid (16.5 mL) with ice cooling. To TEAF was added benzaldehyde (3.78 mL) and 4-hydroxy-chromen-2-one (6.0 g) and the resulting mixture was heated to 130-140° C. for 3 hours, cooled to room temperature, diluted with water, and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4 and conc. in vacuo to give a light yellow solid. The crude solid was recrystallized from EtOH to give 3-Benzyl-4-hydroxy-chromen-2-one as a white solid (1.95 g).

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4 and conc. in vacuo
  5. customto give a light yellow solid
  6. customThe crude solid was recrystallized from EtOH

Sources & evidence

ORD record
ord-2462c7ce65584288b1c7d355e7e74320
Source dataset
uspto-grants-2005_03
Patent number
US06864279B2

Reaction notes

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