Oxalyl chloride → Ethyl 3-[5-(2,5-diisobutoxybenzoyl)-2-isobutoxyphenyl]propanoate

HRID 2249631Notes

Reaction equation

HRID 2249631 reaction equation
[CH2:1]([O:5][C:6]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH:17]([CH3:19])[CH3:18])=[CH:11][C:7]=1[C:8]([OH:10])=O)[CH:2]([CH3:4])[CH3:3].C(Cl)(=O)C(Cl)=O.[Cl-].[Al+3].[Cl-].[Cl-].[CH2:30]([O:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[CH2:41][CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH:31]([CH3:33])[CH3:32]>C(Cl)Cl.C(Cl)(Cl)Cl.CN(C)C=O>[CH2:1]([O:5][C:6]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH:17]([CH3:19])[CH3:18])=[CH:11][C:7]=1[C:8]([C:38]1[CH:39]=[CH:40][C:35]([O:34][CH2:30][CH:31]([CH3:32])[CH3:33])=[C:36]([CH2:41][CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH:37]=1)=[O:10])[CH:2]([CH3:3])[CH3:4]

Participants

8

Reactant 4

HCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 17816468Ethyl 3-(2-isobutoxyphenyl)propanoateHCID 178164772,5-Diisobutoxybenzoic acid

Product 1

HCID 17816548Ethyl 3-[5-(2,5-diisobutoxybenzoyl)-2-isobutoxyphenyl]propanoateYield 98.4%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

In 50 ml of methylene chloride is dissolved 5.00 g of 2,5-diisobutoxybenzoic acid. After adding 2.0 ml of oxalyl chloride and subsequently 20 μl of N,N-dimethylformamide at ambient temperature, the mixture thus obtained is stirred at ambient temperature for one hour. Then, 7.51 g of aluminum chloride and subsequently 5.17 g of ethyl 3-(2-isobutoxyphenyl)-propanoate are added at −30° C., the mixture thus obtained is stirred at −10° C. for 10 minutes. The reaction mixture is added to a mixture of chloroform and ice water and the organic layer is separated. The organic layer thus obtained is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, and the solvent is distilled off under reduced pressure. The residue thus obtained is purified by silica gel column chromatography (eluent; hexane:ethyl acetate=5:1) to obtain 9.21 g of ethyl 3-[5-(2,5-diisobutoxybenzoyl)-2-isobutoxyphenyl]propanoate as a yellow-colored oily product.

Workup

  1. customthe mixture thus obtained
  2. customthe mixture thus obtained
  3. stirringis stirred at −10° C. for 10 minutes
  4. customthe organic layer is separated
  5. customThe organic layer thus obtained
  6. washis washed with water and saturated aqueous solution of sodium chloride successively
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent is distilled off under reduced pressure
  9. customThe residue thus obtained
  10. customis purified by silica gel column chromatography (eluent; hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-bceb32f5e26e44adb92a08ab5636c1cd
Source dataset
uspto-grants-2008_01
Patent number
US07314888B1

Reaction notes

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