Acetic Acid → 3,5-Di-tert-butylsalicylaldehyde

Participants

Reaction Steps

A mixture of 208.4 g (1.0 mol) of 2,4-di-tert-butylphenol and 283.2 g (2.0 mol) of HMT in 500 mL of glacial acetic acid was heated at 130 C. with stirring for 2 hours. A solution of 500 mL of 20% (vol/vol) aqueous sulfuric acid was then added and the resulting solution was refluxed for 0.5 hour. The solution was cooled to around 60°-80° C. and the organic phase was separated from the aqueous phase. The organic phase was recrystallized twice from 150-200 mL of cold (0°-5° C.) methanol to give 93 to 107 g (40-46% yield) of pure 3,5-di-tert-butylsalicylaldehyde of greater than 95% purity by HPLC. mp 60°-62° C. 1H-NMR (60 MHz, CDCl3): δ9.8 (s,1H); 7.6 (d,1H); 7.3 (d,1H); 1.2-1.5 (d,18H). IR (KBr): 3400, 2980, 1650 cm-1.

Provenance & Evidence