2-Methylbenzoic acid → 2-dodecylbenzoic Acid

HRID 2082606Notes

Reaction equation

HRID 2082606 reaction equation
C([N-]C(C)C)(C)C.[Li+].C([Li])CCC.[C:14]1([CH3:23])[C:15]([C:20]([OH:22])=[O:21])=[CH:16][CH:17]=[CH:18][CH:19]=1.[CH2:24](Br)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]>O1CCCC1>[CH2:23]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]([OH:22])=[O:21])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH3:24]

Participants

6

Reactant 4

HCID 83732-Methylbenzoic acidHCID 127441-BromoundecaneHCID 2724682Lithium diisopropylamideHCID 178418339Butyllithium

Product 1

HCID 1224182-dodecylbenzoic Acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution containing lithium diisopropylamide (0.1 mole) was prepared by treating a solution of dissopropylamine (14.1 ml, 0.1 mole) in tetrahydrofuran (200 ml) at 0° C. with n-butyl lithium (41.2 ml of a 2.43M solution, 0.1 mole), and stirring for 5 minutes. To this was added a solution of o-toluic acid (6.8 g, 0.05 mole) in tetrahydrofuran (50 ml). The ice bath was removed and the intense red solution was stirred for 30 minutes. This solution was slowly pipetted into a solution of undecylbromide (11.8 g, 0.05 mole) in tetrahydrofuran (50 ml) at -20° C. After the addition, the cooling bath was removed and the solution stirred for 30 minutes. A small amount of water was added and most of the tetrahydrofuran was removed under reduced pressure. The residue was poured into water, acidified with 3N hydrochloric acid and extracted with ether. The ether was dried, evaporated and the residue was recrystallized from acetonitrile, then from hexane, to give the product.

Workup

  1. customwas prepared
  2. customThe ice bath was removed
  3. stirringthe intense red solution was stirred for 30 minutes
  4. additionAfter the addition
  5. customthe cooling bath was removed
  6. stirringthe solution stirred for 30 minutes
  7. additionA small amount of water was added and most of the tetrahydrofuran
  8. customwas removed under reduced pressure
  9. additionThe residue was poured into water
  10. extractionextracted with ether
  11. dry with materialThe ether was dried
  12. customevaporated
  13. customthe residue was recrystallized from acetonitrile
  14. customfrom hexane, to give the product

Sources & evidence

ORD record
ord-9b5c37b8dec6484cab2105b3290612d7
Source dataset
uspto-grants-1993_02
Patent number
US05189226

Reaction notes

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