Methyl Salicylate → Methyl 2-(2-ethoxy-2-oxoethoxy)benzoate

HRID 636841Notes

Reaction equation

HRID 636841 reaction equation
Cl[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:8]([O:17][CH3:18])(=[O:16])[C:9]1[C:10](=[CH:12][CH:13]=[CH:14][CH:15]=1)[OH:11].C(=O)([O-])[O-].[K+].[K+]>[I-].[K+].C(#N)C>[CH2:6]([O:5][C:3]([CH2:2][O:11][C:10]1[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=1[C:8]([O:17][CH3:18])=[O:16])=[O:4])[CH3:7]

Participants

6

Reactant 3

HCID 4133Methyl SalicylateHCID 7751Ethyl chloroacetateHCID 11430Potassium Carbonate

Product 1

HCID 11806683Methyl 2-(2-ethoxy-2-oxoethoxy)benzoateYield 110.4%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6342AcetonitrileSolvent

Procedure

8020 g (65.44 mol) of ethyl chloroacetate are added to a mixture of 62 l of acetonitrile, 9490 g (62.38 mol) of methyl salicylate, 8610 g (62.38 mol) of potassium carbonate and 620 g of potassium iodide at 20° C., and the mixture is stirred and heated under reflux for 9 hours and stirred overnight without further heat being supplied. The mixture is filtered over Celite and the filtrate is concentrated under reduced pressure. 16.4 kg of methyl 2-ethoxycarbonylmethoxybenzoate are obtained (HPLC: logP=2.1)

Workup

  1. temperatureheated
  2. temperatureunder reflux for 9 hours
  3. stirringstirred overnight
  4. temperaturewithout further heat
  5. filtrationThe mixture is filtered over Celite
  6. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-e37c9da7a4894cd298794e4b8f02ec7f
Source dataset
uspto-grants-2001_02
Patent number
US06194590B1

Reaction notes

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