Allyl bromide → Methyl 5-formyl-2-(1-prop-2-enyloxy)benzoate

HRID 259779Notes

Reaction equation

HRID 259779 reaction equation
[CH:1]([C:3]1[CH:12]=[C:7]([C:8]([O:10][CH3:11])=[O:9])[C:6]([OH:13])=[CH:5][CH:4]=1)=[O:2].[CH2:14](Br)[CH:15]=[CH2:16].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([O:13][CH2:16][CH:15]=[CH2:14])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])=[O:2]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 14363598Methyl 5-Formylsalicylate

Product 1

HCID 18930670Methyl 5-formyl-2-(1-prop-2-enyloxy)benzoateYield 106%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 5-formylsalicylate (3.3 g, 18 mmol), allyl bromide (1.7 mL, 20 mmol), and potassium carbonate (2.8 g, 20 mmol) were stirred at room temperature in DMF (20 mL) overnight. After concentration, the mixture was diluted with EtOAc and extracted with water (5×), then brine. After drying (MgSO4), solvent was removed to give a yellow solid (4.2 g). 1H-NMR(300 MHz, CDCl3): 9.92 (s, 1H), 8.35 (d, 1H, J=2 Hz), 8.00 (dd, 1H, J=9,2 Hz), 7.09 (d, 1H, J=9 Hz), 6.13-6.01 (m, 1H), 5.58-5.34 (m, 2H), 4.75-4.73 (m, 2H), 3.93 (s, 3H). Anal. Calc'd for C12H12O4 : C, 65.45; H, 5.49; Found: C, 65.10; H, 5.36.

Workup

  1. concentrationAfter concentration
  2. additionthe mixture was diluted with EtOAc
  3. extractionextracted with water (5×)
  4. dry with materialAfter drying (MgSO4), solvent
  5. customwas removed

Sources & evidence

ORD record
ord-48fcec3d916d47e8ba06640a79bf49dc
Source dataset
uspto-grants-1996_06
Patent number
US05523302

Reaction notes

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