Methanol → Methyl 3-(3,5-dihydroxyphenyl)prop-2-enoate

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Reaction Steps

FIG. 8 illustrates examples of synthetic schemes for producing alkylated derivatives of 3,5-dihydroxycinnamic acid. In the illustrated synthetic schemes, 3,5-dihydroxycinnamic acid 51 is first esterified in MeOH to produce 3,5-dihydroxycinnamic acid methyl ester 52, which is then reacted with 1 or 2 eq. of an alkylating agent RX in the presence of TBAI and K2CO3 to produce the mono-alkylated intermediate 53 or the dialkylated intermediate 55. The esters 53 and 55 are then hydrolyzed under basic conditions to produce the corresponding acids 54 and 56, respectively.

Provenance & Evidence