Oxalyl chloride → Methyl 2-[5-(2,4-diisobutoxybenzoyl)-2-isobutoxyphenyl]acetate

HRID 2249614Notes

Reaction equation

HRID 2249614 reaction equation
[CH2:1]([O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=O)=[CH:8][C:7]=1[CH2:15][C:16]([O:18][CH3:19])=[O:17])[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]=[C:37]([O:41][CH2:42][CH:43]([CH3:45])[CH3:44])[CH:36]=1)[CH:31]([CH3:33])[CH3:32]>C(Cl)Cl.O.C(Cl)(Cl)Cl>[CH2:42]([O:41][C:37]1[CH:36]=[C:35]([O:34][CH2:30][CH:31]([CH3:33])[CH3:32])[CH:40]=[CH:39][C:38]=1[C:10]([C:9]1[CH:13]=[CH:14][C:6]([O:5][CH2:1][CH:2]([CH3:3])[CH3:4])=[C:7]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:8]=1)=[O:12])[CH:43]([CH3:45])[CH3:44]

Participants

8

Reactant 4

HCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 130875651,3-DiisobutoxybenzeneHCID 178165263-(Methoxycarbonylmethyl)-4-isobutoxybenzoic acid

Product 1

HCID 17816545Methyl 2-[5-(2,4-diisobutoxybenzoyl)-2-isobutoxyphenyl]acetateYield 57.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

In 6 ml of methylene chloride is dissolved 0.62 g of 4-isobutoxy-3-(2-methoxy-2-oxoethyl)benzoic acid. After adding 0.25 ml of oxalyl chloride at ambient temperature, the mixture thus obtained is stirred at ambient temperature for one hour. Then, 0.62 g of aluminum chloride and 0.77 g of 1,3-diisobutoxybenzene are successively added at 5-10° C., and the mixture is stirred at ambient temperature for one hour. The reaction mixture is added to a mixture of chloroform and water, and the organic layer is separated. The organic layer is successively washed with water and saturated aqueous solution of sodium chloride 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; n-hexane:ethyl acetate=95:5] to obtain 0.63 g of methyl 2-[5-(2,4-diisobutoxybenzoyl)-2-isobutoxyphenyl]acetate as a colorless oily product.

Workup

  1. customthe mixture thus obtained
  2. stirringthe mixture is stirred at ambient temperature for one hour
  3. customthe organic layer is separated
  4. washThe organic layer is successively washed with water and saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent is distilled off under reduced pressure
  7. customThe residue thus obtained
  8. customis purified by silica gel column chromatography [eluent; n-hexane:ethyl acetate=95:5]

Sources & evidence

ORD record
ord-74c8718e5dcd4a3d927852690bb3c85f
Source dataset
uspto-grants-2008_01
Patent number
US07314888B1

Reaction notes

Loading…