12-Hydroxystearic acid → 4-Nitro-benzoic acid 11-carboxy-1-hexyl-undecyl ester

HRID 522192

Reaction equation

HRID 522192 reaction equation
[OH:1][CH:2]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14].C(N(CC)CC)C.[N+:29]([C:32]1[CH:40]=[CH:39][C:35]([C:36](Cl)=[O:37])=[CH:34][CH:33]=1)([O-:31])=[O:30]>CC(C)=O>[C:13]([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]([O:1][C:36](=[O:37])[C:35]1[CH:34]=[CH:33][C:32]([N+:29]([O-:31])=[O:30])=[CH:40][CH:39]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])([OH:15])=[O:14]

Participants

5

Reactant 3

HCID 778912-Hydroxystearic acidHCID 8471TriethylamineHCID 85024-Nitrobenzoyl chloride

Product 1

HCID 1183658614-Nitro-benzoic acid 11-carboxy-1-hexyl-undecyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 12-Hydroxy stearic acid (450 grams, 1.5 moles), Triethylamine (313 ml, 2.35 moles) in Acetone (1 L) at 10-15° C., was added 4-Nitro Benzoyl Chloride (332 grams, 1.78 moles) and later stirred at room temperature for 10 hours. 75% of the solvent was distilled off. The resulting solution was cooled to room temperature and poured onto cold water. The pH of the solution was adjusted to 4-5 with dilute HCl, and resulting solid was filtered off and washed with chilled water. The solid was converted into slurry with 500 ml diisopropyl ether. The DIPE was filtered off and the resulting solid was dried in vacuum oven at 70-75° C. to yield pure 4-nitrobenzoic acid 11-carboxy-1-hexyl-undecyl ester product as white powder with a melting point of 98-101° C. The resulting compound was characterized by 1H NMR (DMSO-d6) δ 0.85 (t, 3H, CH3), 1.2-1.6 (m, 28H, 14×CH2), 1.8 (m, 2H, CH2), 2.32 (t, 2H, COCH2), 3.2 (m, 1H, CH) 8.1-8.25 (m, 4H, Ar).

Workup

  1. distillation75% of the solvent was distilled off
  2. temperatureThe resulting solution was cooled to room temperature
  3. additionpoured onto cold water
  4. customresulting solid
  5. filtrationwas filtered off
  6. washwashed with chilled water
  7. filtrationThe DIPE was filtered off
  8. customthe resulting solid was dried in vacuum oven at 70-75° C.

Sources & evidence

ORD record
ord-6b4eb1f098da4874bc872538503fff0c
Source dataset
uspto-grants-2016_05
Patent number
US09328192B2

Linked notes

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