Sodium Hydroxide → 2-(Octadecanoylamino)benzoic acid

HRID 1740760Notes

Reaction equation

HRID 1740760 reaction equation
[OH-].[Na+].[C:3]([NH:22][C:23]1[CH:33]=[CH:32][CH:31]=[CH:30][C:24]=1[C:25]([O:27]CC)=[O:26])(=[O:21])[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][CH2:18][CH2:19][CH3:20]>C(O)C>[C:3]([NH:22][C:23]1[CH:33]=[CH:32][CH:31]=[CH:30][C:24]=1[C:25]([OH:27])=[O:26])(=[O:21])[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][CH2:18][CH2:19][CH3:20]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21832999HCID 21832999, compound

Product 1

HCID 203099812-(Octadecanoylamino)benzoic acidYield 90.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A sodium hydroxide solution (NaOH 0.14 g / water 2 ml) was added to a solution of ethyl 2-(octadecanoylamino)benzoate (1.00 g) in ethanol (10 ml). After being stirred for 4 hours at room temperature, the reaction mixture was concentrated. The residue, with ethyl acetate added thereto, was washed with diluted hydrochloric acid, water and saturated brine successively, dried over sodium sulfate anhydride, and concentrated. The residue was recrystallized from hexane-ethyl acetate mixed solution, thereby yielding 0.85 g of the aimed compound as colorless crystals.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. additionThe residue, with ethyl acetate added
  3. washwas washed with diluted hydrochloric acid, water and saturated brine successively
  4. dry with materialdried over sodium sulfate anhydride
  5. concentrationconcentrated
  6. customThe residue was recrystallized from hexane-ethyl acetate mixed solution

Sources & evidence

ORD record
ord-1191353539cd44619e70dd4382a12025
Source dataset
uspto-grants-1999_10
Patent number
US05972929

Reaction notes

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