1-Bromooctane → octyl levulinate

HRID 2273805Notes

Reaction equation

HRID 2273805 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[C:10]([OH:17])(=[O:16])[CH2:11][CH2:12][C:13]([CH3:15])=[O:14].C([O-])([O-])=O.[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.C1(C)C=CC=CC=1>[C:10]([O:17][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])(=[O:16])[CH2:11][CH2:12][C:13]([CH3:15])=[O:14]

Participants

7

Reactant 3

HCID 81401-BromooctaneHCID 11430Potassium CarbonateHCID 11579Levulinic Acid

Product 1

HCID 11458836octyl levulinate

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

1-Bromooctane (332 g, 1.72 mol) was added to a stirring mixture of levulinic acid (200 g, 1.72 mol), tetrabutylammonium bromide (55.1 g, 0.17 mol), and K2CO3 (357 g, 2.58 mol) in DMF (500 mL) drop-wise and stirred at room temperature for overnight. The resulting mixture was diluted in toluene and the organic layer was washed with HCl (10%), brine, and water. The solvent was concentrated in vacuo and the oil was purified by vacuum distillation to afford the product octyl levulinate as a clear oil.

Workup

  1. washthe organic layer was washed with HCl (10%), brine, and water
  2. concentrationThe solvent was concentrated in vacuo
  3. distillationthe oil was purified by vacuum distillation

Sources & evidence

ORD record
ord-4030913b1b5642dcb54c9c323b5d7e9f
Source dataset
uspto-grants-2015_09
Patent number
US09126890B2

Reaction notes

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