Water → Ethyl 4-chloro-2-(1-(methoxycarbonyl)ethoxy)benzoate

HRID 2399780Notes

Reaction equation

HRID 2399780 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:13])[C:5](=[CH:11][CH:12]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7].C(=O)([O-])[O-].[K+].[K+].Cl[CH:21]([CH3:26])[C:22]([O:24][CH3:25])=[O:23].O>CN(C)C=O>[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:4]([O:13][CH:21]([C:22]([O:24][CH3:25])=[O:23])[CH3:26])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 28659Methyl 2-chloropropionateHCID 12548597Benzoic acid, 4-chloro-2-hydroxy-, ethyl ester

Product 1

HCID 19384699Ethyl 4-chloro-2-(1-(methoxycarbonyl)ethoxy)benzoateYield 62.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 4-chlorosalicylate (9.45 g) and potassium carbonate (10.3 g) in N,N-dimethylformamide (100 ml) was added methyl 2-chloropropionate (6.9 g), followed by stirring overnight at room temperature. The reaction mixture was poured into water (200 ml) and extracted with ether (200 ml×2). The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was subjected to chromatography on silica gel to give ethyl 4-chloro-2-(1(methoxycarbonyl)ethoxy)benzoate (yield, 8.4 g).

Workup

  1. extractionextracted with ether (200 ml×2)
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-043bd56391204da492b4c642e2cbf627
Source dataset
uspto-grants-1995_09
Patent number
US05451607

Reaction notes

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