Ethyl Acetate → Tetradecyl 4-aminobenzoate

HRID 498897

Reaction equation

HRID 498897 reaction equation
[N+:1]([C:4]1[CH:26]=[CH:25][C:7]([C:8]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[O:9])=[CH:6][CH:5]=1)([O-])=O.C(OCC)(=O)C>[Pt].ClCCl>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:8]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[O:9])=[CH:25][CH:26]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 591245Tetradecyl 4-nitrobenzoate

Product 1

HCID 66970570Tetradecyl 4-aminobenzoateYield 65.2%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6344DichloromethaneSolvent

Procedure

Under a nitrogen purge, 10% platinum on carbon (2.5 grams) was added to a mixture of tetradecyl 4-nitrobenzoate (25 grams, 69 mmol) and ethyl acetate (250 milliliters) in a Parr vessel. The vessel was placed under hydrogen pressure (49 psi, 3.3×105 Pa) for sixteen hours. Dichloromethane was added and the reaction mixture was filtered through a layer of CELITE filter aid. The filtrate was concentrated under reduced pressure to a tan solid. The solid was recrystallized from ethanol to obtain 15 grams of tetradecyl 4-aminobenzoate as light tan needles.

Workup

  1. customUnder a nitrogen purge
  2. customfor sixteen hours
  3. filtrationthe reaction mixture was filtered through a layer of CELITE
  4. filtrationfilter aid
  5. concentrationThe filtrate was concentrated under reduced pressure to a tan solid
  6. customThe solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-433343ed12b845bc8669a2281d55ca84
Source dataset
uspto-grants-2010_08
Patent number
US07765698B2

Linked notes

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