Hydrochloric Acid → Isobutyl 3,5-diisobutoxybenzoate

HRID 2249683Notes

Reaction equation

HRID 2249683 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([OH:11])[CH:10]=1)[C:5]([OH:7])=[O:6].C(=O)([O-])[O-].[K+].[K+].[CH2:18](I)[CH:19]([CH3:21])[CH3:20].Cl>CN(C)C=O.O.C(OCC)(=O)C>[CH2:18]([O:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:11][CH2:3][CH:4]([CH3:8])[CH3:5])[CH:10]=1)[C:5]([O:7][CH2:18][CH:19]([CH3:21])[CH3:20])=[O:6])[CH:19]([CH3:21])[CH3:20]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 74243,5-Dihydroxybenzoic AcidHCID 10556Isobutyl iodideHCID 11430Potassium Carbonate

Product 1

HCID 17816465Isobutyl 3,5-diisobutoxybenzoate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

In 50 ml of N,N-dimethylformamide are suspended 5.0 g of 3,5-dihydroxybenzoic acid, 29.8 g of potassium carbonate and 11 ml of isobutyl iodide. The mixture thus obtained is stirred at 110° C. for 7 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 is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, and then the solvent is distilled off under reduced pressure. The residue thus obtained is purified by silica gel column chromatography (eluent; hexane:ethyl acetate=10:1) to obtain 2.6 g of isobutyl 3,5-diisobutoxybenzoate as a light yellow oily product.

Workup

  1. customThe mixture thus obtained
  2. customthe organic layer is separated
  3. washThe organic layer is 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=10:1)

Sources & evidence

ORD record
ord-188b1e095bac4349aebe4e73db85963d
Source dataset
uspto-grants-2008_01
Patent number
US07314888B1

Reaction notes

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