Hexane → 12-(Methoxymethyl)oxy-3,7,11-trimethyl-2,6,10-dodecatrienal

HRID 5669

Reaction equation

HRID 5669 reaction equation
[CH3:1][C:2](O)([CH2:5][CH2:6][CH:7]=[C:8]([CH3:19])[CH2:9][CH2:10][CH:11]=[C:12]([CH3:18])[CH2:13][O:14][CH2:15][O:16][CH3:17])[CH:3]=[CH2:4].[Cr](Cl)([O-])(=O)=[O:22].[NH+]1C=CC=CC=1.CCCCCC.C(OCC)(=O)C>ClCCl.CCOCC>[CH3:17][O:16][CH2:15][O:14][CH2:13][C:12]([CH3:18])=[CH:11][CH2:10][CH2:9][C:8]([CH3:19])=[CH:7][CH2:6][CH2:5][C:2]([CH3:1])=[CH:3][CH:4]=[O:22]

Participants

7

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 541270243,7,11-Trimethyl-12-(methoxymethyl)oxy-1,6,10-dodecatrien-3-olHCID 178418287HCID 178418287, compound

Product 1

HCID 5720638812-(Methoxymethyl)oxy-3,7,11-trimethyl-2,6,10-dodecatrienalYield 52%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 3,7,11-trimethyl-12-(methoxymethyl)oxy-1,6,10-dodecatrien-3-ol (460 mg, 1.6 mmol) in dichloromethane (30 ml) was added pyridinium chlorochromate (690 mg, 3.2 mmol), and the mixture was stirred at room temperature for 8 hours. After addition of a mixture of hexane, ethyl acetate, and ether (3:1:1) (100 ml), the mixture was stirred and insoluble materials were filtered. The filtrate was concentrated in vacuo, and the residue was purified with silica gel column chromatography to give 12-(methoxymethyl)oxy-3,7,11-trimethyl-2,6,10-dodecatrienal (233 mg, 52%). The physico-chemical properties of the product was the same as those described in Reference Example 1.

Workup

  1. stirringthe mixture was stirred
  2. filtrationinsoluble materials were filtered
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-be061f6076814d3eb2e7884b9794b2d8
Source dataset
uspto-grants-1993_09
Patent number
US05245085

Linked notes

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