Methanol → Methyl-P-Coumarate

HRID 2174423Notes

Reaction equation

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

Participants

Reactant 2

HCID 887Methanol

HCID 637542P-Coumaric Acid

Product 1

HCID 5319562Methyl-P-Coumarate

Procedure

Similarly, the monolalkylated derivative of m- or p-coumaric acid can be produced by esterifying coumaric acid in MeOH to produce coumaric acid methyl ester, which is then reacted with an alkylating agent to produce a mono-alkylated intermediate. This intermediate is subsequently hydrolyzed under basic conditions to produce the corresponding alkylated derivative of m- or p-coumaric acid.

Sources & evidence

ORD record: ord-c2cc212b2df14163bceb9ab3121dcad3
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09061993B2

Reaction notes

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