4-Hydroxybenzaldehyde → HCID 20225450, compound

HRID 1719974Notes

Reaction equation

HRID 1719974 reaction equation
[CH2:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8]OS(C1C=CC(C)=CC=1)(=O)=O)[CH:2]=[CH2:3].[OH:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=[O:26])=[CH:23][CH:22]=1.[OH-].[K+]>C(O)C>[CH2:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=[O:26])=[CH:23][CH:22]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 14797Potassium HydroxideHCID 867403431-Butanol, 4-(2-propen-1-yloxy)-, 1-(4-methylbenzenesulfonate)

Product 1

HCID 20225450HCID 20225450, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-allyloxybutyl-p-toluene sulfonate is reacted with p-hydroxybenzaldehyde in the presence of KOH and C2H5OH to form 4-(4-allyloxybutoxy)benzaldehyde which is reacted with malonic acid in the presence of pyridine to form p-(4-allyloxybutoxy)cinnamic acid. The acid is esterified with CH3OH and sulfuric acid to yield the methyl ester, namely methyl p-(4-allyloxybutoxy)cinnamic carboxylate. This methyl ester is then reacted with TosMIC in Et2O/DMSO in the presence of sodium hydride or other strong base to form the substituted pyrrole, represented as follows: ##STR7##

Sources & evidence

ORD record
ord-07c0314329e54620a1e7a11e2a346b8b
Source dataset
uspto-grants-1985_09
Patent number
US04543402

Reaction notes

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