Potassium Hydroxide → 3-Ethylcyclobutane-1,1-dicarboxylic acid

HRID 27293Notes

Reaction equation

HRID 27293 reaction equation
[CH2:1]([CH:3]1[CH2:6][C:5]([C:12]([O:14]CC)=[O:13])([C:7]([O:9]CC)=[O:8])[CH2:4]1)[CH3:2].[OH-].[K+]>C(O)C>[CH2:1]([CH:3]1[CH2:4][C:5]([C:12]([OH:14])=[O:13])([C:7]([OH:9])=[O:8])[CH2:6]1)[CH3:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 20041463Diethyl 3-ethylcyclobutane-1,1-dicarboxylate

Product 1

HCID 200414433-Ethylcyclobutane-1,1-dicarboxylic acidYield 84.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 7.0 g (0.031 mole) of 3-ethyl-1,1-dicarbethoxycyclobutane (prepared in 1C) dissolved in 7 ml of absolute ethanol was prepared. To this solution there was added 6.87 g (0.123 mole) of potassium hydroxide dissolved in 76 ml of absolute ethanol and the mixture was heated to reflux with stirring for 1.5 hr. The mixture was then filtered and the filter cake was washed with 10 ml of absolute ethanol and 75 ml of ether. The resulting filter cake was dissolved in 30 ml of ice water and acidified with 36 ml of 50% aqueous sulfuric acid. The resulting mixture was cooled, filtered and dried to yield 4.5 g of the title compound having the following physical characteristics:

Workup

  1. customwas prepared
  2. temperaturethe mixture was heated
  3. temperatureto reflux
  4. filtrationThe mixture was then filtered
  5. washthe filter cake was washed with 10 ml of absolute ethanol and 75 ml of ether
  6. filtrationThe resulting filter cake
  7. dissolutionwas dissolved in 30 ml of ice water
  8. temperatureThe resulting mixture was cooled
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-07d36e2b18be4e8486728267d48f49c7
Source dataset
uspto-grants-1980_09
Patent number
US04220795

Reaction notes

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