Dimethylformamide → 3,4-Bis(pivalyloxy)phenyl tert-butylaminomethyl ketone

Participants

Reaction Steps

Proceeding in a manner similar to that described in part A of Example 2 above, 17 g. of sodium methoxide was interacted with 26 g. of 3,4-dihydroxyphenyl tert-butylaminomethyl ketone hydrochloride in 200 ml. of N,N-dimethylformamide and the resulting sodium phenolate salt was interacted with 24 g. of pivalyl chloride (alternatively designated as trimethylacetyl chloride or 2,2-dimethylpropanoyl chloride). From this acylation reaction there was obtained 3,4-bis(pivalyloxy)phenyl tert-butylaminomethyl ketone which was treated with hydrochloric acid to yield 11.5 g. of 3,4-bis(pivalyloxy)phenyl tert-butylaminomethyl ketone hydrochloride as a white crystalline solid which melted at 243- 244° C. (dec.)(uncorr.). This salt was soluble in water at 25° C. to the extent of at least 1 per cent.

Provenance & Evidence