Allyl bromide → 1-[2-(Allyloxy)-4-methylphenyl]ethanone

HRID 2406393Notes

Reaction equation

HRID 2406393 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[CH:19]=[CH2:20]>CN(C)C=O>[CH2:20]([O:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10])[CH:19]=[CH2:18]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 813382'-Hydroxy-4'-methylacetophenone

Product 1

HCID 607470631-[2-(Allyloxy)-4-methylphenyl]ethanoneYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(2-hydroxy-4-methyl-phenyl)-ethanone (10 g, 67 mmol) in dimethylformamide (100 mL) was added potassium carbonate (18.4 g, 133 mmol), followed by allyl bromide (5.75 mL, 67 mmol). The reaction was stirred at room temperature for 16 hours. The residue was partitioned between ethyl acetate (200 mL) and water (800 mL), the organics were separated, and washed with brine (50 mL), dried over MgSO4 and concentrated in vacuo. After cooling the concentrate to room temperature the title compound crystallised as colourless platelets, 12.40 g, in a 98% yield. LCMS (2 min acidic) 1.20 min 72-100% pure by UV, ES+/AP+ 191. 1HNMR (400 MHz, CDCl3) δ ppm 2.37 (s, 3H), 2.63 (s, 3H), 4.61-4.66 (m, 2H), 5.33 (dq, 1H), 5.44 (dq, 1H), 6.10 (m, 1H), 6.76 (s, 1H), 6.80-6.83 (m, 1H), 7.68 (d, 1H).

Workup

  1. customThe residue was partitioned between ethyl acetate (200 mL) and water (800 mL)
  2. customthe organics were separated
  3. washwashed with brine (50 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. temperatureAfter cooling the
  7. concentrationconcentrate to room temperature the title compound
  8. customcrystallised as colourless platelets, 12.40 g, in a 98% yield
  9. customLCMS (2 min acidic) 1.20 min 72-100%

Sources & evidence

ORD record
ord-d95407f130594da198f0552523634e33
Source dataset
uspto-grants-2014_08
Patent number
US08809363B2

Reaction notes

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