Synthesis of Vanillin

Reimer-Tiemann & Catechol Pathways

Stable
Validated

Explain the laboratory synthesis of Vanillin from guaiacol and provide the reaction mechanism.

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Vanillin (4-hydroxy-3-methoxybenzaldehyde) can be synthesized through several industrial and laboratory routes. One common laboratory method is the Reimer–Tiemann reaction, though industrially, the glyoxylic acid route from guaiacol is preferred for higher yields.
function Molecular Definition
C_8H_8O_3 \quad \text{(Vanillin)}

Mechanism Overview:

1. ACTIVATION: Guaiacol reacts with glyoxylic acid in an aqueous alkaline medium.

2. CONDENSATION: An electrophilic aromatic substitution occurs at the para-position relative to the hydroxyl group.

GUAIACOL C7H8O2
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VANILLYLMANDELIC ACID Intermediate
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VANILLIN C8H8O3

Sequence: GLYOXYLIC ACID ROUTE

The resulting vanillylmandelic acid is then oxidized (typically with oxygen over a catalyst) to yield Vanillin after acidification and decarboxylation.

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3D Analysis Active
Rotation
Bond Length 1.38 Å AVG
Surface Area 168.4 Ų
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Compound Metadata

Chemical Formula C8H8O3
Molar Mass 152.15 g/mol
PubChem CID 1183
Melting Point 81 - 83 °C
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Purity Match: 99.8%