4-Nitrophenol → 4-Nitrophenyl palmitate

HRID 1580908Notes

Reaction equation

HRID 1580908 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:11](Cl)(=[O:27])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].C(N(CC)CC)C>C(Cl)(Cl)Cl.C(OCC)(=O)C>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11](=[O:27])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 9804-NitrophenolHCID 8206Palmitoyl chlorideHCID 8471Triethylamine

Product 1

HCID 738914-Nitrophenyl palmitate

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 5.0 g of para-nitrophenol in 60 ml of chloroform+ ether (1:1) are added while cooling with ice first 9.4 g of palmitoyl chloride and then 5.0 ml of triethylamine. After having been refluxed for 2 hours, the batch is dissolved in ethyl acetate, and the organic phase is washed with 0.5N-potassium carbonate and water, dried over sodium sulfate and evaporated. On crystallization from ether+petroleum ether, lamellae are obtained which melt at 64°-65°C.

Workup

  1. temperatureAfter having been refluxed for 2 hours
  2. washthe organic phase is washed with 0.5N-potassium carbonate and water
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customOn crystallization from ether+petroleum ether, lamellae
  6. customare obtained which melt at 64°-65°C.

Sources & evidence

ORD record
ord-6cfae4beb74b43e2859427f683f09f45
Source dataset
uspto-grants-1976_01
Patent number
US03934008

Reaction notes

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