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

HRID 2249629Notes

Reaction equation

HRID 2249629 reaction equation
[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([O:15][CH2:16][CH:17]([CH3:19])[CH3:18])[CH:14]=1)[C:9]([OH:11])=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>[CH2:16]([O:15][C:13]1[CH:12]=[C:8]([CH:7]=[C:6]([O:5][CH2:1][CH:2]([CH3:3])[CH3:4])[CH:14]=1)[C:9]([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:11])[CH:17]([CH3:19])[CH3:18]

Participants

8

Reactant 4

HCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 17816468Ethyl 3-(2-isobutoxyphenyl)propanoateHCID 178165213,5-Diisobutoxybenzoic acid

Product 1

HCID 17816456Ethyl 3-[5-(3,5-diisobutoxybenzoyl)-2-isobutoxyphenyl]propanoateYield 84.2%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

In 11 ml of methylene chloride is dissolved 1.11 g of 3,5-diisobutoxybenzoic acid. To the solution thus obtained, 0.44 ml of oxalyl chloride is added at ambient temperature, and then 20 μl of N,N-dimethylformamide is added and stirred at ambient temperature for 2 hours. Then, at −20° C., 1.67 g of aluminum chloride is added and thereafter 1.15 g of ethyl 3-(2-isobutoxyphenyl)propanoate is added, and the mixture thus obtained is stirred at 5-10° 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 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 1.75 g of ethyl 3-[5-(3,5-diisobutoxybenzoyl)-2-isobutoxyphenyl]propanoate as a yellow-colored oily product.

Workup

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

Sources & evidence

ORD record
ord-28672dedda664cd0891949bc994cca2a
Source dataset
uspto-grants-2008_01
Patent number
US07314888B1

Reaction notes

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