Hydrochloric Acid → Ethyl 2-[5-(2,4-diisobutoxybenzoyl)-2-isobutoxyphenoxy]acetate

HRID 2249637Notes

Reaction equation

HRID 2249637 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[C:10]([O:12][CH2:13][CH:14]([CH3:16])[CH3:15])[CH:9]=[CH:8][C:7]=1[C:17]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH:27]([CH3:29])[CH3:28])=[C:21]([OH:30])[CH:20]=1)=[O:18])[CH:2]([CH3:4])[CH3:3].[H-].[Na+].Br[CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36].Cl>CN(C)C=O.O.C(OCC)(=O)C>[CH2:1]([O:5][C:6]1[CH:11]=[C:10]([O:12][CH2:13][CH:14]([CH3:16])[CH3:15])[CH:9]=[CH:8][C:7]=1[C:17]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH:27]([CH3:29])[CH3:28])=[C:21]([CH:20]=1)[O:30][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])=[O:18])[CH:2]([CH3:4])[CH3:3]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 17816454(2,4-Diisobutoxyphenyl)(3-hydroxy-4-isobutoxyphenyl)methanone

Product 1

HCID 17816467Ethyl 2-[5-(2,4-diisobutoxybenzoyl)-2-isobutoxyphenoxy]acetate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

In 9 ml of N,N-dimethylformamide is dissolved 0.86 g of (2,4-diisobutoxyphenyl)(3-hydroxy-4-isobutoxyphenyl)methanone, to which is added 0.12 g of 60% sodium hydride. After elevating the temperature to 80° C., 0.52 ml of ethyl 2-bromoacetate is added, and the mixture thus obtained is stirred at 80-90° C. for 30 minutes. The reaction mixture is cooled to ambient temperature and added to a mixture of ethyl acetate and water, pH is adjusted to 2 with 6 mol/L hydrochloric acid, 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 1.00 g of ethyl 2-[5-(2,4-diisobutoxybenzoyl)-2-isobutoxyphenoxy]acetate as a light yellow oily product.

Workup

  1. customto 80° C.
  2. customthe mixture thus obtained
  3. temperatureThe reaction mixture is cooled to ambient temperature
  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-56bb2acbc1a2485c88f799498f1c4126
Source dataset
uspto-grants-2008_01
Patent number
US07314888B1

Reaction notes

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