Palmitic Acid → 3-Dodecyl-5-isoxazole carboxylic acid

HRID 264103Notes

Reaction equation

HRID 264103 reaction equation
[C:1]([OH:18])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[Na].Cl.[NH2:21][OH:22]>C(O)(=O)C.O>[CH2:5]([C:4]1[CH:3]=[C:2]([C:1]([OH:18])=[O:17])[O:22][N:21]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 3

HCID 985Palmitic AcidHCID 443297Hydroxyamine hydrochlorideHCID 5360545Sodium

Product 1

HCID 106842363-Dodecyl-5-isoxazole carboxylic acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred, warm (55° C.) solution of hexadecanoic acid, 2,4-dioxo, ethyl ester, monosodium salt (15.50 g, 0.046 mol) in glacial acetic acid (125 mL) was added dropwise a solution of hydroxylamine hydrochloride (6.45 g, 0.093 mol) in water (32 mL) over 10 minutes, and the mixture was stirred at 60° C. for 25 hours. The mixture was allowed to cool and partitioned between H2O (250 mL) and chloroform (400 mL). The organic layer was washed (saturated NaCl), dried (MgSO4), and rotoevaporated. The residue was dissolved (toluene), rotoevaporated, and the solid recrystallized from toluene to give a white solid, yield 5.62 g (43%), mp 119°-122° C.

Workup

  1. temperatureto cool
  2. custompartitioned between H2O (250 mL) and chloroform (400 mL)
  3. washThe organic layer was washed (saturated NaCl)
  4. dry with materialdried (MgSO4)
  5. dissolutionThe residue was dissolved (toluene)
  6. customthe solid recrystallized from toluene
  7. customto give a white solid, yield 5.62 g (43%), mp 119°-122° C.

Sources & evidence

ORD record
ord-85ae8511a7864867b5ea6ffd4f82b243
Source dataset
uspto-grants-1997_07
Patent number
US05646170

Reaction notes

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