Dicyclohexylcarbodiimide → 4-Oxo-decanoic acid 3,7-dimethyl-oct-2,6-dienyl ester

HRID 841149

Reaction equation

HRID 841149 reaction equation
[O:1]=[C:2]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH2:3][CH2:4][C:5]([OH:7])=[O:6].[CH3:14][C:15](=[CH:17][CH2:18][CH2:19]/[C:20](=[CH:22]/[CH2:23]O)/[CH3:21])[CH3:16].C1(N=C=NC2CCCCC2)CCCCC1.N1(C2C=CN=CC=2)CCCC1>ClCCl>[CH3:21][C:20]([CH2:19][CH2:18][CH:17]=[C:15]([CH3:16])[CH3:14])=[CH:22][CH2:23][O:6][C:5](=[O:7])[CH2:4][CH2:3][C:2](=[O:1])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 755674-PyrrolidinopyridineHCID 5386474-Oxo capric acidHCID 637566Geraniol

Product 1

HCID 539704894-Oxo-decanoic acid 3,7-dimethyl-oct-2,6-dienyl esterYield 218.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5.2 g 4-oxo-decanoic acid, 13.5 g geraniol, 17.5 g N,N′-dicyclohexyl-carbodiimide and 1.0 g 4-pyrrolidinopyridine in 250 ml of dichloromethane was stirred for 24 hours at room temperature. The precipitate was filtered off, the filtrate was diluted with ether, washed with aqueous hydrochloric acid, saturated NaHCO3 and brine. The organic phase was dried, filtered and evaporated to dryness. The resulting oil-cristall mixture was purified by chromatography to yield 19.7 g of a colourless oil.

Workup

  1. filtrationThe precipitate was filtered off
  2. additionthe filtrate was diluted with ether
  3. washwashed with aqueous hydrochloric acid, saturated NaHCO3 and brine
  4. customThe organic phase was dried
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe resulting oil-cristall mixture was purified by chromatography

Sources & evidence

ORD record
ord-a7d181d12292442e96cf23e8a9f9a07b
Source dataset
uspto-grants-2002_04
Patent number
US06369248B1

Linked notes

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