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

HRID 46955Notes

Reaction equation

HRID 46955 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.CCCCCC>N1C=CC=CC=1>[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 3

HCID 8058HexaneHCID 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 1

HCID 1049PyridineSolvent2×

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-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 white yellow waxy final product. Yield 6.5 g.______________________________________Elementary analysis as C51H77NO2 : C H N______________________________________Theoretical (%): 83.21 10.54 1.90Found (%): 83.18 10.55 1.92______________________________________

Workup

  1. additionthe solution was added with a solution of 4.5 g
  2. additionAfter completion of the addition
  3. customthe reaction
  4. washwashed with water
  5. concentrationconcentrated
  6. customThe concentrate was purified by chromatography with 80 g
  7. washof silica gel in n-hexane/ether solvent mixture as elution solvent

Sources & evidence

ORD record
ord-e739c95e1e404b3f80a62d7e270d12b3
Source dataset
uspto-grants-1979_11
Patent number
US04175139

Reaction notes

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