Hydrogen Peroxide → 3,3',5'-Trimethyl[1,1'-biphenyl]-2-carboxylic acid

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Reaction Steps

The aldehyde 51 (2.75 g, 11.5 mmol) was dissolved in acetonitrile (18 ml, technical grade). NaH2PO4 (0.453 g, dissolved in 5.5 ml H2O) and H2O2 (1.93 ml of a 30% solution) was added. The reaction mixture was cooled to 0° C. (with ice/water) and NaClO2 (2.2 g, dissolved in 19 ml water) was added within 60 min via a syringe. The solution was allowed to warm to ambient temperature and was stirred for additional 3.5 h. Then Na2SO3 (100 mg) was added, stirred for 5 min. After treatment with HCl (50 ml of a 10% solution) the reaction mixture was extracted with ether (3×75 ml). The combined organic phase was extracted with NaOH (4×75 ml, 1 N). The combined NaOH layers were acidified with HCl to pH 1 and extracted again with Et2O. The combined organic layers were dried over MgSO4 and the volatiles removed in vacuo to afford 52 (2.95 g, quant.) as a colorless oil. The product was used without any further purification.

Provenance & Evidence