Nicotinoyl chloride → 3,7,11,15,19,23,27,31,35-Nonamethyl-2,6,10,14,18,22,26,30,34-hexatriacontanonaenyl nicotinate

HRID 2050108Notes

Reaction equation

HRID 2050108 reaction equation
[CH3:1][C:2]([CH3:46])=[CH:3][CH2:4][CH2:5]/[C:6](/[CH3:45])=[CH:7]/[CH2:8][CH2:9]/[C:10](/[CH3:44])=[CH:11]/[CH2:12][CH2:13]/[C:14](/[CH3:43])=[CH:15]/[CH2:16][CH2:17]/[C:18](/[CH3:42])=[CH:19]/[CH2:20][CH2:21]/[C:22](/[CH3:41])=[CH:23]/[CH2:24][CH2:25]/[C:26](/[CH3:40])=[CH:27]/[CH2:28][CH2:29]/[C:30](/[CH3:39])=[CH:31]/[CH2:32][CH2:33]/[C:34](/[CH3:38])=[CH:35]/[CH2:36][OH:37].[C:47](Cl)(=[O:54])[C:48]1[CH:53]=[CH:52][CH:51]=[N:50][CH:49]=1>N1C=CC=CC=1.CCCCCC>[C:47]([O:37][CH2:36][CH:35]=[C:34]([CH3:38])[CH2:33][CH2:32][CH:31]=[C:30]([CH3:39])[CH2:29][CH2:28][CH:27]=[C:26]([CH3:40])[CH2:25][CH2:24][CH:23]=[C:22]([CH3:41])[CH2:21][CH2:20][CH:19]=[C:18]([CH3:42])[CH2:17][CH2:16][CH:15]=[C:14]([CH3:43])[CH2:13][CH2:12][CH:11]=[C:10]([CH3:44])[CH2:9][CH2:8][CH:7]=[C:6]([CH3:45])[CH2:5][CH2:4][CH:3]=[C:2]([CH3:46])[CH3:1])(=[O:54])[C:48]1[CH:53]=[CH:52][CH:51]=[N:50][CH:49]=1

Participants

5

Reactant 2

HCID 82604Nicotinoyl chlorideHCID 5477212Solanesol

Product 1

HCID 30538483,7,11,15,19,23,27,31,35-Nonamethyl-2,6,10,14,18,22,26,30,34-hexatriacontanonaenyl nicotinate

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent2×HCID 8058HexaneSolvent

Procedure

10 Grams of solanesol were dissolved in 50 ml of pyridine and the solution was added with a solution of 4.5 g of nicotinic acid chloride in pyridine dropwise over 30 minutes. After completion of the addition, the mixture was stirred at room temperature for two hours to complete the reaction. The reaction product was diluted with n-hexane, washed with water and concentrated. The concentrate was purified by chromatography with 80 g of silica gel in n-hexane/ether solvent mixture as elution solvent to obtain a white yellow waxy final product.

Workup

  1. additionAfter completion of the addition
  2. customthe reaction
  3. washwashed with water
  4. concentrationconcentrated
  5. customThe concentrate was purified by chromatography with 80 g of silica gel in n-hexane/ether solvent mixture as elution solvent

Sources & evidence

ORD record
ord-e8b587c3ebc84fca94e6296d7a612dea
Source dataset
uspto-grants-1980_04
Patent number
US04199587

Reaction notes

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