Hydrogen Peroxide → 3-(Acetyloxy)-4-isobutoxybenzoic acid

HRID 2249691Notes

Reaction equation

HRID 2249691 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[C:9]([CH:11]=[O:12])[CH:8]=[CH:7][C:6]=1[O:13][CH2:14][CH:15]([CH3:17])[CH3:16])(=[O:3])[CH3:2].P([O-])(O)(O)=[O:19].[Na+].OO.Cl([O-])=O.[Na+]>C(#N)C.O.C(Cl)(Cl)Cl>[C:1]([O:4][C:5]1[CH:10]=[C:9]([CH:8]=[CH:7][C:6]=1[O:13][CH2:14][CH:15]([CH3:17])[CH3:16])[C:11]([OH:19])=[O:12])(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 784Hydrogen PeroxideHCID 178165465-Formyl-2-isobutoxyphenyl acetateHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

Product 1

HCID 178164733-(Acetyloxy)-4-isobutoxybenzoic acidYield 91.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent3×HCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Procedure

In 38 ml of acetonitrile is dissolved 4.1 g of 5-formyl-2-isobutoxyphenyl acetate. To the solution thus obtained, 6.8 g of sodium dihydrogenphosphate dissolved in 20 ml of water and 3.6 ml of 30% aqueous hydrogen peroxide are successively added at ambient temperature, and then 3.6 g of sodium chlorite dissolved in 18 ml of water is dropwise added at 5-10° C. The mixture thus obtained is stirred at ambient temperature for 2 hours. Chloroform and water are added to the reaction mixture, the organic layer is separated, the organic layer thus obtained is washed successively with 5% aqueous solution of sodium thiosulfate and saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and then the solvent is distilled off under reduced pressure. Thus, 4.0 g of 3-(acetyloxy)-4-isobutoxybenzoic acid is obtained as a light yellow solid product.

Workup

  1. customTo the solution thus obtained
  2. additionis dropwise added at 5-10° C
  3. customThe mixture thus obtained
  4. customthe organic layer is separated
  5. customthe organic layer thus obtained
  6. washis washed successively with 5% aqueous solution of sodium thiosulfate and saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-527ad210ab004080907faea5bfbf508c
Source dataset
uspto-grants-2008_01
Patent number
US07314888B1

Reaction notes

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