Potassium Hydroxide → 15-Hydroxypentadecanoic acid

HRID 1532704

Reaction equation

HRID 1532704 reaction equation
[C:1]1(=[O:17])[O:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-:18].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.O>[OH:18][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([OH:16])=[O:17]

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 235414Pentadecalactone

Product 1

HCID 7836015-Hydroxypentadecanoic acidYield 22,360.1%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

15-pentadecanolactone (10 g, 42 mmols), potassium hydroxide (10 g, 0.18 mmols) and tetra-n-butylammonium bromide (1.34 g, 4.2 mmols) were dissolved in a mixed solvent of THF (100 ml) and water (30 ml), and heated under reflux for 12 hours. The reaction mixture was concentrated under reduced pressure to evaporate THF, and the aqueous layer was made acidic (pH=1) and then extracted with ether. The organic layer was washed with water and saturated saline in that order, and dried with anhydrous sodium sulfate, and the solvent was evaporated. The residue was recrystallized from acetone to obtain 10.4 g (yield: 97%) of 15-hydroxypentadecanoic acid as colorless needle-like crystals.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 12 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customto evaporate THF
  5. extractionextracted with ether
  6. washThe organic layer was washed with water and saturated saline in that order
  7. dry with materialdried with anhydrous sodium sulfate
  8. customthe solvent was evaporated
  9. customThe residue was recrystallized from acetone

Sources & evidence

ORD record
ord-b7fa3b7f41de4727a121e60b6128d6a2
Source dataset
uspto-grants-2001_03
Patent number
US06204278B1

Linked notes

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