Benzene → Undecanoic Acid

HRID 1680099Notes

Reaction equation

HRID 1680099 reaction equation
C(O)(=O)C1C=CC=CC=1.C1C=CC=CC=1.[H-].[C:17]([OH:29])(=[O:28])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH:26]=[CH2:27]>C1COCC1>[C:17]([OH:29])(=[O:28])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

6

Reactant 4

HCID 241BenzeneHCID 243Benzoic AcidHCID 5634Undecylenic AcidHCID 166653Hydride

Product 1

HCID 8180Undecanoic Acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Sources & evidence

ORD record
ord-18ee817de0c54112a3b34125b90176d7
Source dataset
uspto-grants-1981_06
Patent number
US04271317

Reaction notes

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