Hydrochloric Acid → 3-(Methoxycarbonylmethyl)-4-isobutoxybenzoic acid

HRID 2249669Notes

Reaction equation

[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([O:14][CH2:15][CH:16]([CH3:18])[CH3:17])=[C:7]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:8]=1)=[O:2].P([O-])(O)(O)=[O:20].[Na+].OO.Cl([O-])=O.[Na+].Cl>C(#N)C.O.C(Cl)(Cl)Cl>[CH3:13][O:12][C:10]([CH2:9][C:7]1[CH:8]=[C:3]([CH:4]=[CH:5][C:6]=1[O:14][CH2:15][CH:16]([CH3:18])[CH3:17])[C:1]([OH:20])=[O:2])=[O:11]

Participants

Conditions

Temperature: 7.5 °C

Procedure

In 8 ml of acetonitrile is dissolved 0.80 g of methyl 2-(5-formyl-2-isobutoxyphenyl)acetate. After successively adding 2.03 g of sodium dihydrogen-phosphate dissolved in 25 ml of water, 0.69 ml of 30% aqueous hydrogen peroxide and 0.73 g of sodium chlorite dissolved in 15 ml of water at a temperature of 5-10° C., the mixture thus obtained is stirred at 5-10° C. for 3.5 hours. Chloroform and water are added to the reaction mixture, pH is adjusted to 2.0 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. Thus, 0.62 g of 3-(methoxycarbonylmethyl)-4-isobutoxybenzoic acid is obtained as a colorless crystalline product.

Workup

customthe mixture thus obtained
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

Sources & evidence

ORD record: ord-b6000604f322432fa50978a2d001169a
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07314888B1

Reaction notes

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