4-Oxopelargonic acid → HCID 54023284, compound

HRID 2304949Notes

Reaction equation

HRID 2304949 reaction equation
[O:1]=[C:2]([CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH2:3][CH2:4][C:5]([OH:7])=[O:6].[CH3:13][C:14](=[CH:16][CH2:17][CH2:18]/[C:19](=[CH:21]/[CH2:22]O)/[CH3:20])[CH3:15]>ClCCl.N1(C2C=CN=CC=2)CCCC1>[CH3:20][C:19]([CH2:18][CH2:17][CH:16]=[C:14]([CH3:15])[CH3:13])=[CH:21][CH2:22][O:6][C:5](=[O:7])[CH2:4][CH2:3][C:2](=[O:1])[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 2

HCID 224334-Oxopelargonic acidHCID 637566Geraniol

Product 1

HCID 54023284HCID 54023284, compoundYield 59.7%

Reagents, catalysts & solvents 2

HCID 755674-PyrrolidinopyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 20 g 4-oxo-nonanoic acid, 19.3 g geraniol, 26.8 g N,N-dicyclohexyl-carbodiimide and 1.0 g 4-pyrrolidinopyridine in 300 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-crystal mixture was purified by chromatography to yield 21.4 g of a colorless 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-crystal mixture was purified by chromatography

Sources & evidence

ORD record
ord-4197acffa2c442a8b35eacf182f34cd1
Source dataset
uspto-grants-2002_08
Patent number
US06437150B1

Reaction notes

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