Oxalyl chloride → 2-(4-Chlorocarbonylphenyl)-2-methylpropionic acid methyl ester

HRID 971164Notes

Reaction equation

HRID 971164 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[C:5](Cl)(=O)[C:6]([Cl:8])=[O:7].[CH3:11][O:12][C:13](=[O:23])[C:14]([CH3:22])([C:16]1[CH:21]=[CH:20]C=[CH:18][CH:17]=1)[CH3:15]>C(Cl)Cl>[CH3:11][O:12][C:13](=[O:23])[C:14]([C:16]1[CH:17]=[CH:18][C:5]([C:6]([Cl:8])=[O:7])=[CH:20][CH:21]=1)([CH3:22])[CH3:15]

Participants

5

Reactant 3

HCID 65578Oxalyl chlorideHCID 143498Methyl 2-methyl-2-phenylpropanoateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 251112122-(4-Chlorocarbonylphenyl)-2-methylpropionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a suspension of AlCl3 (500.0 mg, 3.75 mmol) in CH2Cl2 at −10° C. was added dropwise oxalyl chloride (476.0 mg, 3.75 mmol) in CH2Cl2. The mixture was stirred at this temperature for 30 min. Then a solution of 2-methyl-2-phenyl-propionic acid methyl ester (178.0 mg, 1.0 mmol) in CH2Cl2 was added. The resulted mixture was stirred at −10° C. for 1 hr and rt overnight. The mixture was filtered through a pad of celite, the solvent and excess oxalyl chloride was removed under reduced pressure. The residue was dissolved in chlorobenzene and refluxed for 4 hr. Solvent was removed and the residue was dried to give 2-(4-chlorocarbonyl-phenyl)-2-methyl-propionic acid methyl ester.

Workup

  1. stirringThe resulted mixture was stirred at −10° C. for 1 hr and rt overnight
  2. filtrationThe mixture was filtered through a pad of celite
  3. customthe solvent and excess oxalyl chloride was removed under reduced pressure
  4. dissolutionThe residue was dissolved in chlorobenzene
  5. temperaturerefluxed for 4 hr
  6. customSolvent was removed
  7. customthe residue was dried

Sources & evidence

ORD record
ord-1ae7008a1fbb46c28dc5fd0759be2053
Source dataset
uspto-grants-2007_12
Patent number
US07312214B2

Reaction notes

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