HCID 21159987, compound → cis-Farnesol

HRID 1761761Notes

Reaction equation

HRID 1761761 reaction equation
[CH3:1]/[C:2](/[CH2:9][CH2:10]/[CH:11]=[C:12](/[CH3:19])\[CH2:13][CH2:14][CH:15]=[C:16]([CH3:18])[CH3:17])=[CH:3]/[C:4](OCC)=[O:5].[H-].C([Al+]CC(C)C)C(C)C>C1(C)C=CC=CC=1>[CH3:1]/[C:2](/[CH2:9][CH2:10]/[CH:11]=[C:12](/[CH3:19])\[CH2:13][CH2:14][CH:15]=[C:16]([CH3:18])[CH3:17])=[CH:3]/[CH2:4][OH:5]

Participants

4

Reactant 2

HCID 21159987HCID 21159987, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 1549107cis-Farnesol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 1 g (0.0038 mol) of ethyl (2Z,6Z)-3,7,11-trimethyl-2,6,10-dodecatrienoate in 8 ml of toluene is treated dropwise at -5° to -10° with 9.45 ml of a solution of diisobutylaluminium hydride in toluene (1.2 mol/l, i.e. 3.0 mol equivalents). The solution is stirred at the same temperature for 1 hour under argon. The reaction mixture is poured into an ice-water mixture and extracted with ether. After drying and removing the solvent the residue is chromatographed on silica gel with ether-hexane 1:1. There is obtained (2Z,6Z)-3,7,11-trimethyl-2,6,10-dodecatrien-1-ol which has the following bands in the IR spectrum: 3327 cm-1, 1666 cm-1, 1448 cm-1, 1379 cm-1, 999 cm-1.

Workup

  1. extractionextracted with ether
  2. customAfter drying
  3. customremoving the solvent the residue
  4. customis chromatographed on silica gel with ether-hexane 1:1

Sources & evidence

ORD record
ord-64b67190c7fe4064a06bce0e7867a7b1
Source dataset
uspto-grants-1989_05
Patent number
US04827004

Reaction notes

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