Hydrochloric Acid → 3-Hydroxy-4-isobutoxybenzaldehyde

HRID 2249689Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].C(=O)([O-])[O-].[K+].[K+].[CH2:17](I)[CH:18]([CH3:20])[CH3:19].Cl>CN(C)C=O.O.C(OCC)(=O)C>[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:17][CH:18]([CH3:20])[CH3:19])[CH:5]=[O:6]

Participants

Conditions

Temperature: 80 °C

Procedure

In 50 ml of N,N-dimethylformamide are suspended 5.0 g of 3,4-dihydroxybenzaldehyde, 10.0 g of potassium carbonate and 8.3 ml of isobutyl iodide. The suspension is stirred at 80° 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 then 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 3.3 g of 3-hydroxy-4-isobutoxybenzaldehyde as a light yellow solid product.

Workup

customthe organic layer is separated
customThe organic layer thus obtained
washis 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=5:1)

Sources & evidence

ORD record: ord-7b91aa4cc21e4fbeaebafe06a9041380
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07314888B1

Reaction notes

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