2-Bromo-1'-propionaphthone → 2-Acetoxy-1-(naphth-1-yl)-1-propanone

HRID 33558Notes

Reaction equation

HRID 33558 reaction equation
Br[CH:2]([CH3:15])[C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1)=[O:4].[C:16]([O-:19])(=[O:18])[CH3:17].[Na+]>C(O)C>[C:16]([O:19][CH:2]([CH3:15])[C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1)=[O:4])(=[O:18])[CH3:17]

Participants

4

Reactant 2

HCID 2311612-Bromo-1'-propionaphthoneHCID 517045Sodium Acetate

Product 1

HCID 597968292-Acetoxy-1-(naphth-1-yl)-1-propanone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-bromo-1-(napth-1-yl)-1-propanone (2 g) and sodium acetate (0.63 g) were boiled under reflux in anhydrous ethanol (10 ml) for 16 hours. The mixture was cooled and evaporated in vacuo. The residue was partitioned between ethyl acetate and water. The organic layer was separated, washed with water, brine, dried with sodium sulphate, filtered and evaporated in vacuo. The title compound was obtained as an oil (0.75 g) following silica gel column chromatography of the residue in 50% dichloromethane in petroleum ether.

Workup

  1. temperatureThe mixture was cooled
  2. customevaporated in vacuo
  3. customThe residue was partitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. washwashed with water, brine
  6. dry with materialdried with sodium sulphate
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-2d9742c4ff344484bc7d573efb547a48
Source dataset
uspto-grants-2008_09
Patent number
US07429607B2

Reaction notes

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