Potassium Carbonate → 4-Chloro-2-(2-methoxy-1-methyl-2-oxoethoxy)benzoic acid, methyl ester

HRID 22197

Reaction equation

HRID 22197 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:12])[C:5](=[CH:10][CH:11]=1)[C:6]([O:8][CH3:9])=[O:7].Br[CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][CH:15]([CH3:14])[C:16]([O:18][CH3:19])=[O:17])[CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 76934Methyl 3-bromopropanoateHCID 327085Methyl 4-chloro-2-hydroxybenzoate

Product 1

HCID 867465134-Chloro-2-(2-methoxy-1-methyl-2-oxoethoxy)benzoic acid, methyl esterYield 102.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of methyl 4-chlorosalicylate (5.0 g) in dimethyl formamide (10 ml) was treated sequentially with methyl 3-bromopropionate (4.0 g) and potassium carbonate (6.0 g). The mixture was stirred at room temperature for 18 hrs and diluted with water. The mixture was extracted with ether and the organics were washed with water. The organic layer was dried and evaporated to give the desired material (6.7 g) as a low melting solid. NMR: 7.8 (d, 1H), 7.2 (m 1H), 6.9 (m, 1H), 4.8 (q, 1H), 3.9 (s, 3H), 3.8 (s, 3H), 1.7 (d, 3H).

Workup

  1. extractionThe mixture was extracted with ether
  2. washthe organics were washed with water
  3. customThe organic layer was dried
  4. customevaporated

Sources & evidence

ORD record
ord-91b4768fa10d438db6ef5db0120b996e
Source dataset
uspto-grants-1995_06
Patent number
US05428027

Linked notes

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