Methyl Salicylate → Methyl 2-(1-methoxycarbonylpentoxy)benzoate

HRID 1611054Notes

Reaction equation

HRID 1611054 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].C(=O)([O-])[O-].[K+].[K+].Br[CH:19]([CH2:24][CH2:25][CH2:26][CH3:27])[C:20]([O:22][CH3:23])=[O:21]>C(#N)C>[CH3:23][O:22][C:20]([CH:19]([O:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([O:10][CH3:11])=[O:9])[CH2:24][CH2:25][CH2:26][CH3:27])=[O:21]

Participants

5

Reactant 3

HCID 4133Methyl SalicylateHCID 11430Potassium CarbonateHCID 95578Hexanoic acid, 2-bromo-, methyl ester

Product 1

HCID 10446375Methyl 2-(1-methoxycarbonylpentoxy)benzoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

15.2 g of methyl salicylate and 18.0 g of potassium carbonate were introduced into 125 ml of acetonitrile in a 250 ml flask under an argon atmosphere and, at room temperature, 20.9 g of methyl 2-bromohexanoate were added. The colourless suspension was heated under reflux with stirring for 16 hours, and the progress of the reaction was checked by thin-layer chromatography. After cooling to room temperature, the suspension was filtered and the residue was washed with acetone. Concentration of the filtrate in vacuo resulted in 27.8 g (99% of theory) of methyl 2-(1-methoxycarbonylpentoxy)benzoate as yellow oil.

Workup

  1. temperatureThe colourless suspension was heated
  2. temperatureunder reflux
  3. filtrationthe suspension was filtered
  4. washthe residue was washed with acetone
  5. customConcentration of the filtrate in vacuo resulted in 27.8 g (99% of theory) of methyl 2-(1-methoxycarbonylpentoxy)benzoate as yellow oil

Sources & evidence

ORD record
ord-414dc2d4881d4e1091e5276df4aa6c33
Source dataset
uspto-grants-2006_01
Patent number
US06984741B2

Reaction notes

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