Hexanoic Acid → HCID 20325098, compound

HRID 1518539Notes

Reaction equation

HRID 1518539 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6](O)[C:7]([O:9]CC)=[O:8].C[C:14](C)(C)[C:15]([O-])([O-:17])[O-:16].C(O)(=O)CCCCC.[OH-].[Na+]>C1C2C(CCCC2)CCC1.CO>[C:7]([CH2:6][C:2]1[O:1][CH:5]=[CH:4][C:3]=1[CH2:14][C:15]([OH:17])=[O:16])([OH:9])=[O:8]

Participants

7

Reactant 4

HCID 8892Hexanoic AcidHCID 14798Sodium HydroxideHCID 11446571Ethyl 2-(furan-2-yl)-2-hydroxyacetateHCID 21927715Trimethylorthoacetate

Product 1

HCID 20325098HCID 20325098, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 7044DecalinSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of ethyl 2-(furan-2-yl)-2-hydroxyacetate (11.05 g, 64.5 mmol), trimethylorthoacetate (29.8 mL, 387 mmol) and hexanoic acid (2 mL) in decalin (195 mL) is heated at 180° C. for 12 hours. The reaction is cooled and extracted with methanol to provide a mixture of diester and decalin. This mixture is dissolved in methanol (250 mL), cooled to 0° C., treated with 2 M NaOH (150 mL) and stirred for 12 hours. The methanol is removed and the crude reaction is extracted with ether, and the basic layer is acidified with 6 N HCl and extracted with ethyl acetate. The organic layer is washed with brine, dried and concentrated to give 2,3-di(carboxymethyl)furan.

Workup

  1. temperatureThe reaction is cooled
  2. extractionextracted with methanol
  3. customto provide
  4. customThe methanol is removed
  5. customthe crude reaction
  6. extractionis extracted with ether
  7. extractionextracted with ethyl acetate
  8. washThe organic layer is washed with brine
  9. customdried
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-5b6f81760b5342839dd11d21e55ad893
Source dataset
uspto-grants-2012_07
Patent number
US08232406B2

Reaction notes

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