Potassium Carbonate → Methyl 4-(2-chloroethyl)benzoate

HRID 2288973Notes

Reaction equation

HRID 2288973 reaction equation
[Cl:1][CH2:2][CH2:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1.[C:13]([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[CH3:13][O:9][C:8](=[O:10])[C:7]1[CH:11]=[CH:12][C:4]([CH2:3][CH2:2][Cl:1])=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 887124-(2-Chloroethyl)benzoic acid

Product 1

HCID 22098587Methyl 4-(2-chloroethyl)benzoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-(2-Chloro-ethyl)-benzoic acid (20 g, 108 mmol) in DMF (200 mL) is treated with K2CO3 (59.7 g, 432 mmol) and Mel (16.8 mL, 270 mmol) and stirred at 23 C for 18 h. The reaction mixture is diluted with EtOAc (450 mL) and washed with H2O (2×150 mL), saturated aqueous NaHCO3 (1×200 mL), brine (1×200 mL), dried (MgSO4), and concentrated to afford the title compound as a yellow oil.

Workup

  1. washwashed with H2O (2×150 mL), saturated aqueous NaHCO3 (1×200 mL), brine (1×200 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b6e20fa4256f466195071bcec969ca70
Source dataset
uspto-grants-2000_07
Patent number
US06090825

Reaction notes

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