Octanoic Acid → 5-OCTANOYL-2,2-DIMETHYL-1,3-DIOXANE-4,6-DIONE

HRID 1455167Notes

Reaction equation

HRID 1455167 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[C:16](O)(=[O:24])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].[CH3:26][C:27]1([CH3:35])[O:34][C:32](=[O:33])[CH2:31][C:29](=[O:30])[O:28]1>CN(C)C1C=CN=CC=1.ClCCl>[CH3:26][C:27]1([CH3:35])[O:34][C:32](=[O:33])[CH:31]([C:16](=[O:24])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:29](=[O:30])[O:28]1

Participants

6

Reactant 3

HCID 379Octanoic AcidHCID 10868DicyclohexylcarbodiimideHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 3567035-OCTANOYL-2,2-DIMETHYL-1,3-DIOXANE-4,6-DIONEYield 95%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

N,N′-Dicyclohexylcarbodiimide (11 mmol) was added to a stirred solution of octanoic acid (10 mmol) and 4-dimethylaminopyridine (12 mmol) in dry dichloromethane (40 ml). The mixture was stirred at room temperature for 1 hour and Meldrum's acid (10 mmol) was added. The stirring was continued at room temperature overnight. The solvent was removed in vacuum and the residue redissolved in ethyl acetate and filtered. The filtrate was washed with 2 M HCl solution and dried over MgSO4. The solvent was rotary evaporated to obtain the title product as an oil in 95% yield and was used without purification in the next step.

Workup

  1. waitThe stirring was continued at room temperature overnight
  2. customThe solvent was removed in vacuum
  3. dissolutionthe residue redissolved in ethyl acetate
  4. filtrationfiltered
  5. washThe filtrate was washed with 2 M HCl solution
  6. dry with materialdried over MgSO4
  7. customThe solvent was rotary evaporated

Sources & evidence

ORD record
ord-aea69696d98a498a9eac4c2c44d1489d
Source dataset
uspto-grants-2009_01
Patent number
US07482362B2

Reaction notes

Loading…