Citric Acid → 5-Heptyl-2-oxo-tetrahydro-furan-3-carboxylic acid methylester

HRID 1699986Notes

Reaction equation

HRID 1699986 reaction equation
[CH2:1]([CH:8]1[O:12][C:11](=[O:13])[CH2:10][CH2:9]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[CH3:14][O:15][C:16](=O)[O:17]C.[H-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>>[CH3:14][O:15][C:16]([CH:10]1[CH2:9][CH:8]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])[O:12][C:11]1=[O:13])=[O:17]

Participants

5

Reactant 4

HCID 311Citric AcidHCID 7714Gamma-undecalactoneHCID 12021Dimethyl CarbonateHCID 24758Sodium hydride

Product 1

HCID 154053805-Heptyl-2-oxo-tetrahydro-furan-3-carboxylic acid methylesterYield 56.4%

Conditions

Temperature
65 °C

Procedure

To a mixture of 203 g 5-heptyl-dihydro-furan-2-one and 390 g dimethylcarbonate was slowly added 40 g of sodium hydride. The temperature increased to 65° C. After the temperature returned to room temperature, the reaction mixture was poured into saturated citric acid and extracted with hexane. The organic layer was dried and evaporated to dryness. The residue was distilled to yield 150.5 g of a colourless liquid.

Workup

  1. customreturned to room temperature
  2. extractionextracted with hexane
  3. customThe organic layer was dried
  4. customevaporated to dryness
  5. distillationThe residue was distilled

Sources & evidence

ORD record
ord-5a8ec0eb068a4c4a8ccb93b134cf517e
Source dataset
uspto-grants-2002_02
Patent number
US06348618B1

Reaction notes

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