1-Chloro-3,7-dimethyl-octa-2,6-diene → 4-Hydroxy-undecanoic Acid 3,7-dimethyl-octa-2,6-dienyl Ester

HRID 1169178Notes

Reaction equation

HRID 1169178 reaction equation
Cl[CH2:2][CH:3]=[C:4]([CH3:11])[CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9].[Na+].[OH:13][CH:14]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:15][CH2:16][C:17]([O-:19])=[O:18]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[CH3:11][C:4]([CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])=[CH:3][CH2:2][O:19][C:17](=[O:18])[CH2:16][CH2:15][CH:14]([OH:13])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 2

HCID 991061-Chloro-3,7-dimethyl-octa-2,6-dieneHCID 23710311Sodium 4-hydroxyundecanoate

Product 1

HCID 542694794-Hydroxy-undecanoic Acid 3,7-dimethyl-octa-2,6-dienyl EsterYield 31.8%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 155 g 1-chloro-3,7-dimethyl-octa-2,6-diene, 202 g 4-hydroxy-undecanoic acid sodium salt and 5 g tetrabutylammoniumbromide in 800 ml of dimethylformamide was heated to 50° C. After stirring for 24 hours, the mixture was cooled to room temperature and filtered through Celite. The filtrate was diluted with ether, washed with water, 2N HCl, saturated sodium bicarbonate and brine. The organic phase was dried and evaporated to dryness. The resulting yellow oil was purified by wipe film distillation to yield 96.6 g of a yellow oil.

Workup

  1. temperaturethe mixture was cooled to room temperature
  2. filtrationfiltered through Celite
  3. additionThe filtrate was diluted with ether
  4. washwashed with water, 2N HCl, saturated sodium bicarbonate and brine
  5. customThe organic phase was dried
  6. customevaporated to dryness
  7. customThe resulting yellow oil was purified
  8. distillationfilm distillation

Sources & evidence

ORD record
ord-417d0397852244dea67db1b06c058be2
Source dataset
uspto-grants-2003_09
Patent number
US06627763B2

Reaction notes

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