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

HRID 716726Notes

Reaction equation

HRID 716726 reaction equation
[C:1]([O:4][CH2:5][CH2:6]Cl)(=[O:3])[CH3:2].[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+]>CN(C=O)C>[CH2:5]([O:4][C:1](=[O: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])[CH3:6]

Participants

5

Reactant 3

HCID 4133Methyl SalicylateHCID 10959beta-Chloroethyl acetateHCID 11430Potassium Carbonate

Product 1

HCID 11806683Methyl 2-(2-ethoxy-2-oxoethoxy)benzoateYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Chloroethyl acetate was slowly added to a mixture of methyl salicylate (100 g, 0.657 mol) and K2CO3 (100 g, 0.723 mol) in DMF (400 mL) at ambient temperature (20-30° C.). The reaction mixture was heated at 65-75° C. for 12-18 h. The progress of the reaction was monitored by HPLC analysis. Upon completion of reaction, the inorganics were filtered off and washed with DMF. DMF was recovered from the filtrate to obtain the product meeting the desired specifications. Yield—91-95%.

Workup

  1. customUpon completion of reaction
  2. filtrationthe inorganics were filtered off
  3. washwashed with DMF
  4. customDMF was recovered from the filtrate
  5. customto obtain the product

Sources & evidence

ORD record
ord-948bd99434e64eb4b73345c83a8aa7e1
Source dataset
uspto-grants-2015_11
Patent number
US09193698B2

Reaction notes

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