4-Nitrophenol → Hexadec-2-enoic acid

HRID 1780682Notes

Reaction equation

HRID 1780682 reaction equation
O[CH:2]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:3][C:4]([OH:6])=[O:5].C(OC(=O)C)(=O)C.[N+](C1C=CC(O)=CC=1)([O-])=O.C1(N=C=NC2CCCCC2)CCCCC1>N1C=CC=CC=1.CN(C)C=O.C(Cl)(Cl)Cl.O>[C:4]([OH:6])(=[O:5])[CH:3]=[CH:2][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

8

Reactant 4

HCID 9804-NitrophenolHCID 7918Acetic AnhydrideHCID 10868DicyclohexylcarbodiimideHCID 3015903-Hydroxyhexadecanoic acid

Product 1

HCID 152802Hexadec-2-enoic acidYield 49.3%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6228DimethylformamideSolventHCID 22418719Chloroform waterSolvent

Procedure

To a solution of 3-hydroxyhexadecanoic acid (2 g) in pyridine was added acetic anhydride at 0° C., and the mixture was stirred for 4 hours. The reaction mixture was distributed into chloroform-water, and the chloroform layer was concentrated. The residue obtained was dissolved in N,N-dimethylformamide (DMF). Para-nitrophenol (1.02 g) and N,N'-dicyclohexylcarbodiimide (1.51 g) were added to the solution, and the mixture was stirred for 12 hours. The reaction mixture was filtered and concentrated, and the residue was subjected to chromatography on a silica gel column with eluent systems of n-hexane-ethyl acetate (from 100:1 to 50:1) to give an active ester of 2-hexadecenoic acid (0.92 g) and an active ester of 3-acetoxyhexadecanoic acid (1.01 g).

Workup

  1. concentrationthe chloroform layer was concentrated
  2. customThe residue obtained
  3. stirringthe mixture was stirred for 12 hours
  4. filtrationThe reaction mixture was filtered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1ae227b827ff4e2c9fd5bb5f6dd20489
Source dataset
uspto-grants-1997_05
Patent number
US05631238

Reaction notes

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