Toluene → 4-Methoxyphenylacetic Acid

HRID 1358090Notes

Reaction equation

HRID 1358090 reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:2].[Na+].[Na+].[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH:21]=[O:22])=[CH:16][CH:15]=1.C1(C)C=CC=CC=1>O>[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]([OH:2])=[O:22])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 25408Sodium DichromateHCID 797824-Methoxyphenylacetaldehyde

Product 1

HCID 76904-Methoxyphenylacetic AcidYield 9,896.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

1.44 equivalents (7.7 g) of sodium periodate NaIO4, 0.6 mol % (0.045 g) of sodium dichromate Na2Cr2O72H2O and 3 g of 1N sulfuric acid H2SO4 (12 mol %) were dissolved in 50 ml of water. To this solution were added 25 mmol (3.75 g) of 4-methoxyphenylacetaldehyde and 25 ml of toluene, whereupon the reaction mixture was stirred for 17 h at 20° C. The phases were then separated and the aqueous phase was extracted with 2×10 ml of toluene. 30 ml of 1N NaOH were added to the combined toluene phases. The basic water phase was made acidic with 3 g of conc. H2SO4 and extracted with 2×25 ml of toluene. The combined organic phases were washed 3× with H2O, dried over Na2SO4 and evaporated to dryness. 17 mmol (2.82 g) of p-methoxyphenylacetic acid (yield 68% of theory) with a purity of 98% were obtained.

Workup

  1. customThe phases were then separated
  2. extractionthe aqueous phase was extracted with 2×10 ml of toluene
  3. addition30 ml of 1N NaOH were added to the combined toluene phases
  4. extractionextracted with 2×25 ml of toluene
  5. washThe combined organic phases were washed 3× with H2O
  6. dry with materialdried over Na2SO4
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-126f9ab144b54b49bdfd2f843f051018
Source dataset
uspto-grants-2003_07
Patent number
US06593494B2

Reaction notes

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