Diethyl Ether → P-Toluic Acid

HRID 13740

Reaction equation

HRID 13740 reaction equation
Br([O-])(=O)=O.[Na+].[CH3:6][C:7]1[CH:14]=[CH:13][C:10]([CH2:11][OH:12])=[CH:9][CH:8]=1.CC[O:17]CC>C(#N)C.O>[CH3:6][C:7]1[CH:14]=[CH:13][C:10]([C:11]([OH:17])=[O:12])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 115054-Methylbenzyl alcoholHCID 23668195Sodium Bromate

Product 1

HCID 7470P-Toluic AcidYield 96%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Conditions

Temperature
80 °C

Procedure

A mixture of Ceiv catalyst from Example 47 (0.08 g), sodium bromate (0.3 g) and 4-methylbenzyl alcohol (0.24 g, 2 mmol) in acetonitrile:water (1:1, 10 ml) was stirred at 80° C. for 40 h under an atmosphere of nitrogen. On cooling ether (70 ml) was added and the catalyst was filtered off. The organic layer was separated and the aqueous phase was extracted with ether (2×50 ml). The combined organic extracts were washed with water (25 ml), dried with anhydrous magnesium sulphate and concentrated to give 4-methylbenzoic acid as a white solid (0.26 g, 96%). M.p. 178° C., lit. 180-182° C.

Workup

  1. additionwas added
  2. filtrationthe catalyst was filtered off
  3. customThe organic layer was separated
  4. extractionthe aqueous phase was extracted with ether (2×50 ml)
  5. washThe combined organic extracts were washed with water (25 ml)
  6. dry with materialdried with anhydrous magnesium sulphate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3a9fbafd96bf492091f8f6f9a3668ff1
Source dataset
uspto-grants-2010_06
Patent number
US07728159B2

Linked notes

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