4-Hydroxybenzaldehyde

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4-Hydroxybenzaldehyde
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Template:Longitem Template:Chembox Elements/molecular formula
Molar mass Template:Chem molar mass
Appearance yellow to tan powder
Density 1.129 g/cm3 (130 °C)[1]
Melting point Template:Chembox CalcTemperatures
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Acidity (pKa) 7.61 (25 °C)[3]
Template:Longitem −78.0·10−6 cm3/mol
Template:Longitem 1.57051 (130 °C)[1]

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4Template:NbhHydroxy­benzaldehyde (paraTemplate:Nbhhydroxy­benzaldehyde) is an organic compound with the formula Template:Chem2.[4][5] Along with 2-hydroxybenzaldehyde and 3-hydroxybenzaldehyde, it is one of the three isomers of hydroxybenzaldehyde.

Synthesis, reactions, uses

4-Hydroxybenzaldehyde is prepared by reaction of phenol with chloroform, which gives isomeric hydroxybenzal chlorides. Hydrolysis of the C-Cl bonds gives the aldehyde.[5]

4-Hydroxybenzaldehyde is a precursor to 4-hydroxyphenylglycine, a precursor to penicillins. In the Dakin oxidation, 4-hydroxybenzaldehyde reacts with hydrogen peroxide in base to form hydroquinone.

Metabolism and occurrence

p-Hydroxybenzaldehyde dehydrogenase is an enzyme found in carrots (Daucus carota).[6]

4-Hydroxybenzaldehyde is found in the orchids Gastrodia elata,[7] Galeola faberi,[8] and the Vanilla orchids.

See also

References

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  1. a b c Haynes, p. 3.304
  2. Haynes, p. 5.154
  3. Haynes, p. 5.92
  4. Merck Index, 11th Edition, 8295
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Cited sources

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