Farnesol → (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienal

HRID 1010514Notes

Reaction equation

HRID 1010514 reaction equation
C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.[OH:12][CH2:13]/[CH:14]=[C:15](/[CH2:17][CH2:18]/[CH:19]=[C:20](/[CH2:22][CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26])\[CH3:21])\[CH3:16]>ClCCl>[CH3:26][C:25]([CH3:27])=[CH:24][CH2:23][CH2:22]/[C:20](/[CH3:21])=[CH:19]/[CH2:18][CH2:17]/[C:15](/[CH3:16])=[CH:14]/[CH:13]=[O:12]

Participants

4

Reactant 2

HCID 445070FarnesolHCID 178418287HCID 178418287, compound

Product 1

HCID 5280598(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienalYield 73.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 15 g of PCC in 250 mL of dichloromethane was added 10 g of (E,E)-farnesol (1). The reaction mixture was stirred at room temperature overnight and filtered through a 55-cm (height) by 5-cm (diameter) column of silica gel. The eluate was dried over MgSO4, and the solvent was removed by rotary evaporation to give a greenish-yellow oil. The crude farnesal was purified by column chromatography (silica gel/chloroform) to yield 7.25 g of product 2, predominantly the (E,E)-isomer. 1H NMR δ (ppm) 10.0 (d, CHO), 5.9 (d, CH2C(CH3)═CHCO), 5.1 (t, CH3C(CH3)═CH and CH2C(CH3)═CH), 2.3 (m, CH2C(CH3)═CH—CO), 2.5 (m, CH2C(CH3)═CHCH2CH2), 2.2 (s, CH3C═CH—CO), 2.0 (m, CH3C(CH3)═CHCH2CH2), 1.6-1.7 (all s, CH3C(CH3)═CHCH2CH2CCH3).

Workup

  1. filtrationfiltered through a 55-cm (height) by 5-cm (diameter) column of silica gel
  2. dry with materialThe eluate was dried over MgSO4
  3. customthe solvent was removed by rotary evaporation
  4. customto give a greenish-yellow oil
  5. customThe crude farnesal was purified by column chromatography (silica gel/chloroform)

Sources & evidence

ORD record
ord-8dc9f0fb5a634977aea988df727dd2e9
Source dataset
uspto-grants-2011_07
Patent number
US07977315B2

Reaction notes

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