Methyl Salicylate → HCID 69098843, compound

HRID 1027873Notes

Reaction equation

HRID 1027873 reaction equation
[C:1]([O:10][CH3:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].Br[CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[CH3:11][O:10][C:1](=[O:9])[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[O:4][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

6

Reactant 4

HCID 4133Methyl SalicylateHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrate

Product 1

HCID 69098843HCID 69098843, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

Methyl salicylate (4.6 g, 30 mmol) was treated with ethyl 4-bromobutyrate (6.5 g, 33 mmol) followed by the addition of potassium carbonate (4.6 g, 33 mmol), potassium iodide (61 mg, 0.36 mmol) and acetone (75 mL). The mixture was heated at reflux for 16 hours, cooled and filtered to remove the solids. The solids were washed with additional acetone and the combined filtrates were concentrated under reduced pressure. The residue was dissolved in ether (150 mL), cooled to 0° C., washed with 40 mL of 0.5 M sodium hydroxide, washed with brine, dried (MgSO4), filtered, concentrated under reduced pressure and the residue chromatographed on silica gel eluting with a gradient of hexane:EtOAc (10:1, 5:1 and 4:1) to provide the title compound. 1H NMR (CDCl3) δ 1.25 (t, J=7.12 Hz, 3H), 2.09-2.22 (m, 2H), 2.59 (t, J=7.29 Hz, 2H), 3.89 (s, 3H), 4.06-4.19 (m, 4H), 6.93-7.03 (m, J=8.14, 8.14 Hz, 2H), 7.40-7.48 (m, 1H), 7.78 (dd, J=7.63, 1.86 Hz, 1H); MS (M+H)+ m/z 267.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 16 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. customto remove the solids
  6. washThe solids were washed with additional acetone
  7. concentrationthe combined filtrates were concentrated under reduced pressure
  8. dissolutionThe residue was dissolved in ether (150 mL)
  9. washwashed with 40 mL of 0.5 M sodium hydroxide
  10. washwashed with brine
  11. dry with materialdried (MgSO4)
  12. filtrationfiltered
  13. concentrationconcentrated under reduced pressure
  14. customthe residue chromatographed on silica gel eluting with a gradient of hexane:EtOAc (10:1, 5:1 and 4:1)

Sources & evidence

ORD record
ord-752e20debad34c368a1936813b349d95
Source dataset
uspto-grants-2014_05
Patent number
US08735411B2

Reaction notes

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