Benzene → Undecanoic Acid

Participants

Reaction Steps

Extended reflux of carboxylic acids with excess thexylborane-THF is known to give aldehydes. By contrast TBDA at 0° C. reduces aliphatic carboxylic acids to give predominantly the corresponding alcohols. Benzoic acid in THF is only reduced to the extent of 15% in 48 hours whereas in benzene 1.98 equivalents of hydride are taken up in 2.5 hours. 10-Undecenoic acid reacts only at the double bond with one equivalent of TBDA at 0° C. in 15 minutes. Hydrolysis of the intermediate organoborane gives undecanoic acid in 90% isolated yield.

Provenance & Evidence