Hydrochloric Acid → HCID 53663281, compound

HRID 2258040Notes

Reaction equation

HRID 2258040 reaction equation
[CH3:1][C:2]([CH2:7][CH2:8][CH:9]=[C:10]([CH3:37])[CH2:11][CH2:12][CH:13]=[C:14]([CH3:36])[CH2:15][CH2:16][CH:17]=[C:18]([CH3:35])[CH2:19][CH2:20][CH:21]=[C:22]([CH3:34])[CH2:23][CH2:24][CH:25]=[C:26]([CH3:33])[CH2:27][CH2:28][CH:29]=[C:30]([CH3:32])[CH3:31])=[CH:3][C:4]([OH:6])=[O:5].[Na].O.Cl>CCCCCO>[CH3:1][CH:2]([CH2:7][CH2:8][CH:9]=[C:10]([CH3:37])[CH2:11][CH2:12][CH:13]=[C:14]([CH3:36])[CH2:15][CH2:16][CH:17]=[C:18]([CH3:35])[CH2:19][CH2:20][CH:21]=[C:22]([CH3:34])[CH2:23][CH2:24][CH:25]=[C:26]([CH3:33])[CH2:27][CH2:28][CH:29]=[C:30]([CH3:32])[CH3:31])[CH2:3][C:4]([OH:6])=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 5360545Sodium2×HCID 53899776HCID 53899776, compound

Product 1

HCID 53663281HCID 53663281, compound

Reagents, catalysts & solvents 1

HCID 62761-PentanolSolvent

Procedure

82 g of 3,7,11,15,19,23,27-heptamethyl-2,6,10,14,18,22,26-octacosaheptaenoic acid was dissolved in 1 l of n-amyl alcohol and 74 g of metallic sodium was added portionwise while the solution was vigorously stirred. After metallic sodium was completely dissolved, the reaction solution was poured into iced water and was made acidic by adding 300 ml of 6N hydrochloric acid. It was then extracted with 1 l of n-hexane, washed with water, dried and concentrated. 78 g of colorless, oily 3,7,11,15,19,23,27-heptamethyl-6,10,14,18,22,26-octacosahexaenoic acid was obtained as the crude product. The product was then added dropwise to 500 ml of an ethereal suspension of 10 g of lithium aluminum hydride while being cooled by ice and stirred. After stirring was continued for 30 minutes, 10 ml of water with 10 ml of a 15% caustic soda solution, and 30 ml of water were sequentially added. The precipitated crystal was filtered and washed twice with 200 ml of ether. The filtrate was concentrated and the concentrate was defined by silica gel column chromatography, providing the captioned 3,7,11,15,19,23,27-heptamethyl-6,10,14,18,22,26-octacosahexaenol as a colorless oily matter.

Workup

  1. extractionIt was then extracted with 1 l of n-hexane
  2. washwashed with water
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-89a14ceedb724f8886c454908e9d6023
Source dataset
uspto-grants-1997_08
Patent number
US05658958

Reaction notes

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