Diethyl Ether → 9-Octadecenal, (9Z)-

HRID 344765

Reaction equation

HRID 344765 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[CH2:12]([OH:30])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]/[CH:20]=[CH:21]\[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].CCOCC>ClCCl>[CH:12](=[O:30])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]/[CH:20]=[CH:21]\[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 5284499Oleyl AlcoholHCID 178418287HCID 178418287, compound

Product 1

HCID 53644929-Octadecenal, (9Z)-Yield 90.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

An 18 g portion of pyridinium chlorochromate was slurried in 200 ml of dichloromethane. A solution of 15 g of oleyl alcohol in 200 ml of dichloromethane was added. This mixture was stirred for 4 hours, then poured into ether and filtered through hydrous magnesium silicate. The filtrate was evaporated, giving 13.42 g of the desired compound as a colorless liquid.

Workup

  1. filtrationfiltered through hydrous magnesium silicate
  2. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-0a27b92f0b3f46f8b3c80fea1702af49
Source dataset
uspto-grants-1991_10
Patent number
US05053426

Linked notes

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