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

HRID 2249669
Notes
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Reaction equation

HRID 2249669 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 17816550Methyl 2-(5-formyl-2-isobutoxyphenyl)acetateHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

Product 1

HCID 178165263-(Methoxycarbonylmethyl)-4-isobutoxybenzoic acidYield 72.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent3×HCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

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

  1. customthe mixture thus obtained
  2. customthe organic layer is separated
  3. customThe organic layer thus obtained
  4. washis washed with water and saturated aqueous solution of sodium chloride successively
  5. dry with materialdried over anhydrous magnesium sulfate
  6. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes