Reaction #42018

Reaction equation

sodium bromate

4-methylbenzyl alcohol

ether

→

4-methylbenzoic acid

Yield 96.0%

Solvents

acetonitrile water

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   Filtrationthe catalyst was filtered off
3. 3
   OtherThe organic layer was separated
4. 4
   Extractionthe aqueous phase was extracted with ether (2×50 ml)
5. 5
   WashThe combined organic extracts were washed with water (25 ml)
6. 6
   Dryingdried with anhydrous magnesium sulphate
7. 7
   Concentrationconcentrated

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.

Source