Hydrochloric Acid → HCID 53838961, compound

HRID 1595694Notes

Reaction equation

HRID 1595694 reaction equation
[CH3:1][C:2]([CH2:6][CH2:7][CH:8]=[C:9]([CH3:41])[CH2:10][CH2:11][CH:12]=[C:13]([CH3:40])[CH2:14][CH2:15][CH:16]=[C:17]([CH3:39])[CH2:18][CH2:19][CH:20]=[C:21]([CH3:38])[CH2:22][CH2:23][CH:24]=[C:25]([CH3:37])[CH2:26][CH2:27][CH:28]=[C:29]([CH3:36])[CH2:30][CH2:31][CH:32]=[C:33]([CH3:35])[CH3:34])=[CH:3][C:4]#[N:5].CO.[Na].Cl>C1COCC1>[CH3:1][CH:2]([CH2:6][CH2:7][CH:8]=[C:9]([CH3:41])[CH2:10][CH2:11][CH:12]=[C:13]([CH3:40])[CH2:14][CH2:15][CH:16]=[C:17]([CH3:39])[CH2:18][CH2:19][CH:20]=[C:21]([CH3:38])[CH2:22][CH2:23][CH:24]=[C:25]([CH3:37])[CH2:26][CH2:27][CH:28]=[C:29]([CH3:36])[CH2:30][CH2:31][CH:32]=[C:33]([CH3:35])[CH3:34])[CH2:3][C:4]#[N:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 5360545SodiumHCID 54519280HCID 54519280, compound

Product 1

HCID 53838961HCID 53838961, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

21 g of 3,7,11,15,19,23,27,31-octamethyl-2,6,10,14,18,22,26,30-dotriacontaoctaenonitrile was dissolved in250 ml of methanol and 100 ml of THF, and 24 g of metallic sodium was added. The reaction solution was stirred at room temperature for 30 minutes and was cooled with ice when foaming and heat generation were recognized. After the reaction solution was reacted for 2 hours, 500 ml of 6N hydrochloric acid was added and the reaction product was extracted by 500 ml of n-hexane. The organic layer was concentrated and the concentrate was refined by silica gel column chromatography, providing 16 g of 3,7,11,15,19,23,27,31-octamethyl-6,10,14,18,22,26,30-dotriacontaheptaenonitrile.

Workup

  1. additionwas added
  2. temperaturewas cooled with ice when
  3. temperatureheat generation
  4. customAfter the reaction solution was reacted for 2 hours
  5. extractionthe reaction product was extracted by 500 ml of n-hexane
  6. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-93436fe135f842e6bffa51fab7d6a58c
Source dataset
uspto-grants-2001_09
Patent number
US06288128B1

Reaction notes

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