Pyridine → HCID 11200948, compound

HRID 40422

Reaction equation

HRID 40422 reaction equation
[CH2:1]([OH:19])[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][CH2:16][CH2:17][CH3:18].N1C=CC=CC=1.[N+:26]([C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1)([O-:28])=[O:27]>ClCCl>[N+:26]([C:29]1[CH:30]=[CH:31][C:32]([C:33]([O:19][CH2:1][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][CH2:16][CH2:17][CH3:18])=[O:34])=[CH:36][CH:37]=1)([O-:28])=[O:27]

Participants

5

Reactant 3

HCID 1049PyridineHCID 8221Stearyl AlcoholHCID 85024-Nitrobenzoyl chloride

Product 1

HCID 11200948HCID 11200948, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

Under a nitrogen atmosphere, a mixture of 1-octadecanol (36 grams, 210 mmol), pyridine (20 milliliters), and dichloromethane (500 milliliters) was heated to reflux. The alcohol dissolved and the solution was allowed to cool 5° C. 4-Nitrobenzoyl chloride (39.0 grams, 210 mmol) was added in portions over a twenty minute period. The reaction mixture was heated to reflux for sixteen hours. The reaction mixture was washed with 250 milliliters of water. The aqueous layer was washed with 250 milliliters of dichloromethane. The organic layers were combined and concentrated under reduced pressure to a light tan solid. Added 500 milliliters of hexane and heated to reflux. A white precipitate formed as the solution was cooled to room temperature. Filtered off the white precipitate and concentrated the filtrate to a light tan solid. The solid was recrystallized from ethanol (500 milliliters) to obtain 46 grams of octadecyl 4-nitrobenzoate as a white solid.

Workup

  1. temperaturewas heated to reflux
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux for sixteen hours
  4. washThe reaction mixture was washed with 250 milliliters of water
  5. washThe aqueous layer was washed with 250 milliliters of dichloromethane
  6. concentrationconcentrated under reduced pressure to a light tan solid
  7. additionAdded 500 milliliters of hexane
  8. temperatureheated to reflux
  9. customA white precipitate formed as the solution
  10. temperaturewas cooled to room temperature
  11. filtrationFiltered off the white precipitate
  12. concentrationconcentrated the filtrate to a light tan solid
  13. customThe solid was recrystallized from ethanol (500 milliliters)

Sources & evidence

ORD record
ord-ae0cee8c1a6a4930922007ad5c59d4ac
Source dataset
uspto-grants-2013_09
Patent number
US08529671B2

Linked notes

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