Formic Acid → Ethyl 7-(2-hydroxy-5-oxocyclopent-3-en-1-yl)heptanoate

HRID 616855Notes

Reaction equation

HRID 616855 reaction equation
[C:1]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12](O)[C:13]1[O:17][CH:16]=[CH:15][CH:14]=1)([O:3][CH2:4][CH3:5])=[O:2].C(O)=[O:20].C([O-])=O.[Na+].C1(C=CC(O)=CC=1)O>O1CCOCC1.O>[C:1]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]1[CH:13]([OH:17])[CH:14]=[CH:15][C:16]1=[O:20])([O:3][CH2:4][CH3:5])=[O:2]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 785HydroquinoneHCID 2723810Sodium FormateHCID 14142143HCID 14142143, compound

Product 1

HCID 22165421Ethyl 7-(2-hydroxy-5-oxocyclopent-3-en-1-yl)heptanoate

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

A stirred mixture of 2.0g (7.87 mmol) of α-(6-carbethoxyhexyl)furfuryl alcohol (Example 4), 5.93 ml of 97% formic acid, 268 mg of sodium formate, 10 mg of hydroquinone, and 40 ml of 3:2 dioxane-water is stirred at reflux for 18 hr. The solution is cooled, saturated with salt, and extracted with ether. The extract is washed with brine, dried over magnesium sulfate, and concentrated to give an amber oil.

Workup

  1. temperatureat reflux for 18 hr
  2. temperatureThe solution is cooled, saturated with salt
  3. extractionextracted with ether
  4. washThe extract is washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customto give an amber oil

Sources & evidence

ORD record
ord-64bb7f9bac5d4e708434b8553e15d131
Source dataset
uspto-grants-1978_02
Patent number
US04076732

Reaction notes

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