ChemicalBook CAS DataBase List 4-Hydroxybenzaldehyde

4-Hydroxybenzaldehyde synthesis

13synthesis methods

Product Name:4-Hydroxybenzaldehyde
CAS Number:123-08-0
Molecular formula:C7H6O2
Molecular Weight:122.12

Prepared by heating sodium phenolate with carbon dioxide under pressure.

Methanediol,1-[4-(acetyloxy)phenyl]-, 1,1-diacetate

7143-16-0
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123-08-0
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Yield:123-08-0 96%

Reaction Conditions:

with ethanol at 50 - 60; for 0.0833333 h;

Steps:

2.3. General procedure for the deprotection of 1,1-diacetates

General procedure: A mixture of the 1,1-diacetate of the aldehyde (5 mmol) andP(4-VPH)ClO4 (20 mg) in ethanol (5 mL) was stirred at 50-60°C. Upon completion of the reaction (as determined by TLC),the mixture was filtered to remove the catalyst. The filtrate wascollected and distilled to dryness to give a residue, which waspartitioned between water (10 mL) and Et2O (5 mL). The etherlayer was collected and the aqueous layer was back-extractedwith Et2O (2 × 5 mL). The combined ether layers were washedwith a saturated solution of NaHCO3 (5 mL) and dried overanhydrous Na2SO4. The solvent was removed under vacuum togive the crude product as a residue, which was purified by silicagel column chromatography (n-hexane:ethyl acetate = 85:15(v/v)) to afford the pure aldehyde.

References:

Khaligh, Nader Ghaffari [Cuihua Xuebao/Chinese Journal of Catalysis,2014,vol. 35,# 3,p. 329 - 334]