4-decylbenzaldehyde

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: General procedure G was used to couple 1-decene (8.1 mmol) to 4-bromobenzaldehyde (5.4 mmol) to yield 1.25 g (5.1 mmol) of the title product after column chromatography. Spectral data was consistent with previously reported compounds.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Rosenmund Reduction--Hydrogenate a mixture of 4-(n-decyl)benzoyl chloride (28 g., 0.1 mol), 10% palladium on carbon (2 g.), 2,6-lutidine (10.9 g., dried over KOH and distilled), and tetrahydrofuran (THF) (300 ml., distilled from LiAlH4) in a Paar apparatus for 30 min. at 25° C. under an H2 atmosphere (62 psi). Filter the resulting mixture and collect the catalyst. Wash the catalyst with THF. Evaporate the filtrate and partition the residue between diethyl ether and H2O. Wash the combined organic solutions with aqueous HCl (0.1N) and NaHCO3 (0.1N) solutions. Evaporate the solvent from the dried organic solution to give a liquid. Distill the liquid to give 4-(n-decyl)benzaldehyde (19 g. 77% yield, b.p. 152°-156° C. at 0.3 mm). Filter the resulting mixture collect the catalyst Wash the catalyst with THF Evaporate the filtrate partition the residue between diethyl ether and H2O Wash the combined organic solutions with aqueous HCl (0.1N) and NaHCO3 (0.1N) solutions Evaporate the solvent from the dried organic solution to give a liquid Distill the liquid