Acetone → HCID 54283770, compound

HRID 1596719Notes

Reaction equation

HRID 1596719 reaction equation
[OH:1][C:2]1[CH:3]=[C:4](C(=O)C)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Br[CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].C([O-])([O-])=O.[K+].[K+].[CH3:34][C:35](C)=[O:36]>>[C:35]([C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[C:7]([O:8][CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:6]=1)(=[O:36])[CH3:34]

Participants

5

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 106816281-(4-(Benzyloxy)-3-hydroxyphenyl)ethanone

Product 1

HCID 54283770HCID 54283770, compound

Procedure

A solution of 3′-hydroxy4′-benzyloxyacetophenone (3.5 g, 14.4 mmol), t-butyl bromoacetate (2.8 mL, 17.0 mmol), and K2CO3 (2.3 g, 17.0 mmol) in 100 mL acetone is refluxed 18 hours. After cooling, the mixture is filtered, and the acetone is removed in vacuo. The residue is then dissolved in EtOAc (50 mL) and washed with H2O (1×50 mL) and brine (1×50 mL), dried over MgSO4, and the solvent is removed in vacuo. Chromatography (silica, 5:1 hexane/EtOAc) yields t-butyl (4-acetyl-2-benzyloxyphenoxy)-acetate.

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture is filtered
  3. customthe acetone is removed in vacuo
  4. dissolutionThe residue is then dissolved in EtOAc (50 mL)
  5. washwashed with H2O (1×50 mL) and brine (1×50 mL)
  6. dry with materialdried over MgSO4
  7. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-2efe9644eecf4fa3800788b87d9ada90
Source dataset
uspto-grants-2001_09
Patent number
US06291530B1

Reaction notes

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