Water → 4-Nitro-benzoic acid 11-carboxy-1-hexyl-undec-3-enyl ester

HRID 522190

Reaction equation

HRID 522190 reaction equation
[C:1]([OH:21])(=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][C@@H:12]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[OH:13].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].O>CC(C)=O>[C:1]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH:10][CH2:11][CH:12]([O:13][C:36](=[O:37])[C:35]1[CH:34]=[CH:33][C:32]([N+:29]([O-:31])=[O:30])=[CH:40][CH:39]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])([OH:21])=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 643684Ricinoleic Acid

Product 1

HCID 1317355124-Nitro-benzoic acid 11-carboxy-1-hexyl-undec-3-enyl esterYield 31.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of ricinoleic acid (1600 g), triethylamine (1100 mL) in acetone (6 L) at 0-5° C., was added 4-nitro benzoyl chloride (1200 g). It was stirred at room temperature for 16 hours. After the reaction was completed then the total reaction mass was poured onto cold water (12 L) and extracted with ethyl acetate (6 liter) and combined total organic layers and washed with 15% NaHCO3 solution (IL) and 15% NaCl solution (1.0 L) followed by water washing (1.0 L), then dry the organic layer with sodium sulphate and distilled up the solvent under reduced pressure completely till thick oily mass is obtained. Resulting crude was purified by column chromatography by using hexane: ethyl acetate (9:1) to yield pure 4-nitro-benzoic acid 11-carboxy-1-hexyl-undec-3-enyl ester product as light yellow thick syrup (750 g). The resulting compound was characterized by 1H NMR (DMSO-d6) δ 0.85 (t, 3H, CH3), 1.12-1.6 (m, 22H, 11×CH2), 1.91 (m, 2H, CH2), 2.2-2.32 (m, 4H, 2×CH2), 3.5 (m, 1H, CH) 5.52 (m, 1H, CH), 5.65 (m, 1H, CH), 8.25-8.35 (m, 4H, Ar).

Workup

  1. extractionextracted with ethyl acetate (6 liter)
  2. washwashed with 15% NaHCO3 solution (IL) and 15% NaCl solution (1.0 L)
  3. dry with materialdry the organic layer with sodium sulphate
  4. distillationdistilled up the solvent under reduced pressure completely till thick oily mass
  5. customis obtained
  6. customResulting crude
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-6602755ceae34d169aa21c144994995a
Source dataset
uspto-grants-2016_05
Patent number
US09328192B2

Linked notes

Loading…