Hydrochloric Acid → Methyl 2-[5-(4-isobutoxy-2-isopentyloxybenzoyl)-2-isobutoxyphenyl]acetate

HRID 2249626Notes

Reaction equation

HRID 2249626 reaction equation
[OH:1][C:2]1[CH:25]=[C:24]([O:26][CH2:27][CH:28]([CH3:30])[CH3:29])[CH:23]=[CH:22][C:3]=1[C:4]([C:6]1[CH:7]=[CH:8][C:9]([O:17][CH2:18][CH:19]([CH3:21])[CH3:20])=[C:10]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:11]=1)=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH2:37](I)[CH2:38][CH:39]([CH3:41])[CH3:40].Cl>CN(C)C=O.O.C(OCC)(=O)C>[CH2:27]([O:26][C:24]1[CH:23]=[CH:22][C:3]([C:4]([C:6]2[CH:7]=[CH:8][C:9]([O:17][CH2:18][CH:19]([CH3:21])[CH3:20])=[C:10]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:11]=2)=[O:5])=[C:2]([O:1][CH2:37][CH2:38][CH:39]([CH3:41])[CH3:40])[CH:25]=1)[CH:28]([CH3:30])[CH3:29]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 109241-Iodo-3-methylbutaneHCID 11430Potassium CarbonateHCID 17816483Methyl 2-[5-(2-hydroxy-4-isobutoxybenzoyl)-2-isobutoxyphenyl]acetate

Product 1

HCID 17816460Methyl 2-[5-(4-isobutoxy-2-isopentyloxybenzoyl)-2-isobutoxyphenyl]acetate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

In 3 ml of N,N-dimethylformamide are suspended 0.28 g of methyl 2-[5-(2-hydroxy-4-isobutoxybenzoyl)-2-isobutoxyphenyl]acetate, 0.32 g of potassium carbonate and 0.23 ml of isopentyl iodide. The suspension is stirred at 120° C. for 2 hours. The reaction mixture is 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 0.17 g of methyl 2-[5-(4-isobutoxy-2-isopentyloxybenzoyl)-2-isobutoxyphenyl]-acetate as a colorless oily product.

Workup

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

Sources & evidence

ORD record
ord-ea1a440b465a47cda21db825488e9385
Source dataset
uspto-grants-2008_01
Patent number
US07314888B1

Reaction notes

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