a Farnesol → Farnesyl farnesyl carboxylate

HRID 463526Notes

Reaction equation

HRID 463526 reaction equation
[CH2:1]([C:16]([OH:18])=[O:17])[CH:2]=[C:3]([CH2:5][CH2:6][CH:7]=[C:8]([CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])[CH3:9])[CH3:4].O[CH2:20][CH:21]=[C:22]([CH2:24][CH2:25][CH:26]=[C:27]([CH2:29][CH2:30][CH:31]=[C:32]([CH3:34])[CH3:33])[CH3:28])[CH3:23].C(N(CC)CC)C.[I-].ClC1C=CC=C[N+]=1C>C1(C)C=CC=CC=1>[CH2:1]([C:16]([O:18][CH2:20][CH:21]=[C:22]([CH2:24][CH2:25][CH:26]=[C:27]([CH2:29][CH2:30][CH:31]=[C:32]([CH3:33])[CH3:34])[CH3:28])[CH3:23])=[O:17])[CH:2]=[C:3]([CH2:5][CH2:6][CH:7]=[C:8]([CH2:10][CH2:11][CH:12]=[C:13]([CH3:14])[CH3:15])[CH3:9])[CH3:4]

Participants

6

Reactant 4

HCID 3327a FarnesolHCID 8471TriethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 537917614,8,12-Trimethyltrideca-3,7,11-trienoic acid

Product 1

HCID 3047772Farnesyl farnesyl carboxylateYield 78.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of farnesyl carboxylic acid (5.0 g), farnesol (4.44 g) and triethylamine (4.85 g) was added dropwise at room temperature to a stirred solution of 2-chloro-1-methylpyridinium iodide (5.61 g) in 40 ml of toluene. After complete addition, the reaction mixture was heated on boiled water bath for three hours. After cooling, the mixture was washed with water and dried (Na2SO4). The solvent was removed in vacuo and gave a pale yellow oil. This material was purified by silica gel chromatography by using n-hexane and gave 7.15 g of the titled compound.

Workup

  1. additionAfter complete addition
  2. temperaturethe reaction mixture was heated
  3. customfor three hours
  4. temperatureAfter cooling
  5. washthe mixture was washed with water
  6. dry with materialdried (Na2SO4)
  7. customThe solvent was removed in vacuo
  8. customgave a pale yellow oil
  9. customThis material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-fadfbf9cb2b5402a9d2bf31d88c66dcd
Source dataset
uspto-grants-1985_05
Patent number
US04520029

Reaction notes

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