Pyridine → Tetradecyl 4-nitrobenzoate

HRID 40420

Reaction equation

HRID 40420 reaction equation
[CH2:1]([OH:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].N1C=CC=CC=1.[N+:22]([C:25]1[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[CH:27][CH:26]=1)([O-:24])=[O:23]>ClCCl>[N+:22]([C:25]1[CH:26]=[CH:27][C:28]([C:29]([O:15][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][CH3:14])=[O:30])=[CH:32][CH:33]=1)([O-:24])=[O:23]

Participants

5

Reactant 3

HCID 1049PyridineHCID 82091-TetradecanolHCID 85024-Nitrobenzoyl chloride

Product 1

HCID 591245Tetradecyl 4-nitrobenzoateYield 47.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
30 °C

Procedure

Under a nitrogen atmosphere, a mixture of 1-tetradecanol (96.3 grams, 449 mmol), pyridine (40 milliliters), and dichloromethane (1000 milliliters) was heated to 30° C. 4-Nitrobenzoyl chloride (100 grams, 539 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 water (2×500 milliliters). The organic layer was concentrated under reduced pressure to a yellow solid. 1000 milliliters of hexane was added and the mixture was heated to reflux. The mixture was cooled and filtered. The filtrate was concentrated to yield a yellow solid. The yellow solid was recrystallized twice from ethanol to obtain 77.0 grams of tetradecyl 4-nitrobenzoate as yellow crystals.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for sixteen hours
  3. washThe reaction mixture was washed with water (2×500 milliliters)
  4. concentrationThe organic layer was concentrated under reduced pressure to a yellow solid
  5. addition1000 milliliters of hexane was added
  6. temperaturethe mixture was heated to reflux
  7. temperatureThe mixture was cooled
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated
  10. customto yield a yellow solid
  11. customThe yellow solid was recrystallized twice from ethanol

Sources & evidence

ORD record
ord-b35a550697104ceb8fa76ba10f219eba
Source dataset
uspto-grants-2013_09
Patent number
US08529671B2

Linked notes

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