Hydrochloric Acid → Isobutyl 2,5-diisobutoxybenzoate

HRID 2249685Notes

Reaction equation

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

Participants

Conditions

Temperature: 110 °C

Procedure

In 200 ml of N,N-dimethylformamide are suspended 10 g of 2,5-dihydroxybenzoic acid, 148 g of potassium carbonate and 106 ml of isobutyl bromide. The mixture is stirred at 110° C. for 6 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 18 g of isobutyl 2,5-diisobutoxybenzoate as a light yellow oily product.

Workup

customthe organic layer is separated
washThe organic layer is washed with water and saturated aqueous solution of sodium chloride successively
dry with materialdried over anhydrous magnesium sulfate
distillationthe solvent is distilled off under reduced pressure
customThe residue thus obtained
customis purified by silica gel column chromatography (eluent; hexane:ethyl acetate=10:1)

Sources & evidence

ORD record: ord-c26bb5fe7a1b4882b9bd548466166847
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07314888B1

Reaction notes

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