Acetylresorcinol → 3-(allyloxy)phenyl Acetate

HRID 1370829Notes

Reaction equation

HRID 1370829 reaction equation
[C:1]([O:4][C:5]1[CH:11]=[CH:10][CH:9]=[C:7]([OH:8])[CH:6]=1)(=[O:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH2:18](Br)[CH:19]=[CH2:20]>CN(C=O)C.C(OCC)(=O)C>[C:1]([O:4][C:5]1[CH:11]=[CH:10][CH:9]=[C:7]([O:8][CH2:20][CH:19]=[CH2:18])[CH:6]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 5055AcetylresorcinolHCID 7841Allyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 112755383-(allyloxy)phenyl AcetateYield 57%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Resorcinol monoacetate (10.0 g, 65.7 mmoles) in anhydrous DMF (100 mL) was treated with K2CO3 (18.2 g, 131 mmoles) and allyl bromide (6.83 mL, 78.9 mmoles). The mixture was heated at 80° C. overnight, cooled to room temperature, and diluted with ethyl acetate. The mixture was washed with H2O, brine, dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, 8% to 10% ethyl acetate:hexanes) to provide the title compound as a colorless oil (7.19 g, 57%). MS (DCI) m/z 193 (M+H)+.

Workup

  1. temperaturecooled to room temperature
  2. washThe mixture was washed with H2O, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure
  6. customThe residue was purified by flash chromatography (silica gel, 8% to 10% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-f14c00b350ee42cc9a468fae3c3d7105
Source dataset
uspto-grants-2003_06
Patent number
US06583180B2

Reaction notes

Loading…