4-Hydroxybenzaldehyde → 4-Coumaric acid

HRID 1719973Notes

Reaction equation

HRID 1719973 reaction equation
[C:1]([OH:7])(=[O:6])[CH2:2][C:3](O)=O.[OH:8][C:9]1[CH:16]=[CH:15][C:12](C=O)=[CH:11][CH:10]=1>CCOCC>[OH:8][C:9]1[CH:16]=[CH:15][C:12]([CH:3]=[CH:2][C:1]([OH:7])=[O:6])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 1264-HydroxybenzaldehydeHCID 867Malonic Acid

Product 1

HCID 3224-Coumaric acid

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Sometimes it is convenient to derive the ether substituent from the hydroxyphenyl substituent at the same position the latter occupies, for example, in the following sequence of steps. Malonic acid and p-hydroxybenzaldehyde are reacted to form p-hydroxycinnamic acid, followed by esterification with methanol in the presence of conc H2SO4 to form the methyl ester. This ester is then reacted with TosMIC in the presence of NaH to form methyl 4-hydroxyphenylpyrrole-3-carboxylate ("P-carboxylate"). The P-carboxylate is then reduced with LiAlH4 in THF to the 3-methyl-4-hydroxyphenylpyrrole which is then reacted with allyloxybutyl bromide to yield the 4-(4-allyloxybutoxyphenyl-3-methyl-pyrrole.

Sources & evidence

ORD record
ord-d2b35e82020f4ae3ad78902e4ed50a0c
Source dataset
uspto-grants-1985_09
Patent number
US04543402

Reaction notes

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