Hydrochloric Acid → 3,5-Diisobutoxybenzoic acid

HRID 2249684Notes

Reaction equation

HRID 2249684 reaction equation
[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([CH:16]=[C:17]([O:19][CH2:20][CH:21]([CH3:23])[CH3:22])[CH:18]=1)[C:9]([O:11]CC(C)C)=[O:10])[CH:2]([CH3:4])[CH3:3].[OH-].[Na+].C(Cl)(Cl)Cl.Cl>CO.O>[CH2:20]([O:19][C:17]1[CH:16]=[C:8]([CH:7]=[C:6]([O:5][CH2:1][CH:2]([CH3:4])[CH3:3])[CH:18]=1)[C:9]([OH:11])=[O:10])[CH:21]([CH3:23])[CH3:22]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 14798Sodium HydroxideHCID 17816465Isobutyl 3,5-diisobutoxybenzoate

Product 1

HCID 178165213,5-Diisobutoxybenzoic acidYield 87.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

In 13 ml of methanol is dissolved 2.5 g of isobutyl 3,5-diisobutoxybenzoate, to which is then added 2.3 ml of 5 mol/L sodium hydroxide solution. The mixture thus obtained is stirred at 50° C. for 3 hours. Chloroform and water are added to the reaction mixture, 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. Thus, 1.8 g of 3,5-diisobutoxybenzoic acid is obtained as a white solid 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

Sources & evidence

ORD record
ord-de732816561e4a21a0495977400ad866
Source dataset
uspto-grants-2008_01
Patent number
US07314888B1

Reaction notes

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