Benzyl Bromide → 6-(Benzyloxy)chroman-4-one

HRID 1886087Notes

Reaction equation

HRID 1886087 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH2:7][CH2:6][C:5]2=[O:12].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O.CCOC(C)=O>[CH2:13]([O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH2:7][CH2:6][C:5]2=[O:12])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 70989446-Hydroxy-chroman-4-one

Product 1

HCID 144227766-(Benzyloxy)chroman-4-one

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 6-hydroxy-4-chromanone (18.6 g, 113 mmol), benzyl bromide (20 g, 116 mmol), and K2CO3 (21 g, 152 mmol) in acetone (110 ml) was refluxed for 20 hrs. The mixture was cooled, diluted with EtOAc, and filtered through celite. The filtrate was concentrated to an oil, which was triturated with 10% Et2O in hexane (150 ml) to gives, after filtration and washing, 28 g (87%) of the title compound.

Workup

  1. temperaturewas refluxed for 20 hrs
  2. temperatureThe mixture was cooled
  3. filtrationfiltered through celite
  4. concentrationThe filtrate was concentrated to an oil, which
  5. customwas triturated with 10% Et2O in hexane (150 ml)
  6. customto gives
  7. filtrationafter filtration
  8. washwashing

Sources & evidence

ORD record
ord-daf93f38cc334e4da1a6fd3b1de8daeb
Source dataset
uspto-grants-1992_09
Patent number
US05149703

Reaction notes

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