Palmitoyl chloride → HCID 11108028, compound

HRID 463641Notes

Reaction equation

HRID 463641 reaction equation
[C:1](Cl)(=[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].C1C=CN=CC=1.[FH:25]>>[C:1]([F:25])(=[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]

Participants

3

Reactant 2

HCID 8206Palmitoyl chlorideHCID 64774Pyridine, hydrofluoride (1:1)

Product 1

HCID 11108028HCID 11108028, compoundYield 76%

Conditions

Temperature
20 °C

Procedure

Palmitoyl chloride (651 mg, 2.2 mole) was added to pyridinium poly(hydrogen fluoride) (1 ml) in a teflon reaction vial and the mixture stirred at 20° C. for 20 min. After cooling to 0° C., it was quenched with ice-water (5 ml), extracted with ethyl acetate, and the organic layer washed (water, brine), dried over anhydrous magnesium sulfate, concentrated and evaporatively distilled (120° C./0.025 torr) to give palmitoyl fluoride (76%) (contaminated with 5% of the corresponding acid). Since this concentration of contaminant is not harmful to the biological activity of the compound, no further purification is required.

Workup

  1. temperatureAfter cooling to 0° C.
  2. customit was quenched with ice-water (5 ml)
  3. extractionextracted with ethyl acetate
  4. washthe organic layer washed (water, brine)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. distillationevaporatively distilled (120° C./0.025 torr)

Sources & evidence

ORD record
ord-65295d1451aa4ea089dfab470ceec9da
Source dataset
uspto-grants-1985_10
Patent number
US04544504

Reaction notes

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