Sodium Carbonate → HCID 5463066, compound

HRID 1259009Notes

Reaction equation

HRID 1259009 reaction equation
[CH2:1]([OH:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl.CCOC(C)=O>[CH:1](=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 5365682Linoleyl alcoholHCID 178418287HCID 178418287, compound

Product 1

HCID 5463066HCID 5463066, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of linoleyl alcohol (15 g, 56 mmol) in anhydrous CH2Cl2 (400 mL) was treated with pyridinium chlorochromate (36.4 g, 169 mmol) and Na2CO3 (2.98 g, 28.2 mmol) and then stirred (4 h). The reaction mixture was diluted with EtOAc and filtered through a pad of silica and then concentrated. The crude material was subjected to chromatography (1%→3%→6% EtOAc-heptane) to yield (9Z,12Z)-octadeca-9,12-dienal (10.5 g, 71%) as a colorless oil. Rf 0.58 (10% EtOAc-hexanes), FW 264.45, C18H32O.

Workup

  1. filtrationfiltered through a pad of silica
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-2c1503afd61a46b394e6f40641b1f20a
Source dataset
uspto-grants-2013_06
Patent number
US08466122B2

Reaction notes

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