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

HRID 2174422Notes

Reaction equation

HRID 2174422 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([OH:13])[CH:12]=1)[CH:5]=[CH:6][C:7]([OH:9])=[O:8].[CH3:14]O>>[CH3:14][O:8][C:7](=[O:9])[CH:6]=[CH:5][C:4]1[CH:3]=[C:2]([OH:1])[CH:12]=[C:11]([OH:13])[CH:10]=1

Participants

3

Reactant 2

HCID 887MethanolHCID 19363128374-93-8

Product 1

HCID 67111031Methyl 3-(3,5-dihydroxyphenyl)prop-2-enoate

Procedure

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.

Sources & evidence

ORD record
ord-f4e707b96b7c48498dbb32cb154dab22
Source dataset
uspto-grants-2015_06
Patent number
US09061993B2

Reaction notes

Loading…