Hydrochloric Acid → HCID 54203058, compound

HRID 850947Notes

Reaction equation

HRID 850947 reaction equation
[CH3:1][C:2]([CH2:9][CH2:10][CH:11]=[C:12]([CH3:24])[CH2:13][CH2:14][CH:15]=[C:16]([CH3:23])[CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])=[CH:3][CH2:4][CH2:5][C:6](=[O:8])[CH3:7].[BH4-].[Na+].Cl>CO>[CH3:1][C:2]([CH2:9][CH2:10][CH:11]=[C:12]([CH3:24])[CH2:13][CH2:14][CH:15]=[C:16]([CH3:23])[CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])=[CH:3][CH2:4][CH2:5][CH:6]([OH:8])[CH3:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 53996,10,14,18-Tetramethylnonadeca-5,9,13,17-tetraen-2-oneHCID 4311764Sodium borohydride

Product 1

HCID 54203058HCID 54203058, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1 g of 6,10,14,18-tetramethyl-5,9,13,17-nonadecatetraene-2-on was dissolved in 20 ml. of methanol. 60 mg of sodium borohydride was added to the solution and the whole was stirred for 30 minutes. The reaction liquid was poured in ice-water. Dilute hydrochloric acid solution was added thereto to make the same acidic. The liquid was then subjected to the extraction with 50 ml. of n-hexane. The extract was washed with water and dried with magnesium sulfate. The solvent was distilled out to obtain 1 g of an oily product. The product was purified according to silica gel column chromatography to obtain 0.95 g of the intended product in the form of a colorless oil from 10% ether/n-hexane effluent.

Workup

  1. customThe reaction liquid
  2. extractionThe liquid was then subjected to the extraction with 50 ml
  3. washThe extract was washed with water
  4. dry with materialdried with magnesium sulfate
  5. distillationThe solvent was distilled out

Sources & evidence

ORD record
ord-d24bc5b256e04a74b6d7d58fcc50c036
Source dataset
uspto-grants-1983_05
Patent number
US04382151

Reaction notes

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