Sodium Hydroxide → 1-(Ethoxycarbonyl)cyclobutane-1-carboxylic acid

HRID 35270Notes

Reaction equation

HRID 35270 reaction equation
[OH-].[Na+].[C:3]1([C:12]([O:14]CC)=[O:13])([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:6][CH2:5][CH2:4]1>C(O)C>[CH2:10]([O:9][C:7]([C:3]1([C:12]([OH:14])=[O:13])[CH2:4][CH2:5][CH2:6]1)=[O:8])[CH3:11]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 77410Diethyl 1,1-cyclobutanedicarboxylate

Product 1

HCID 105591051-(Ethoxycarbonyl)cyclobutane-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium hydroxide (1N, 22.5 mmol) was added dropwise (1 drop for every 20 seconds) to a stirred solution of diethyl 1,1-cyclobutanedicarboxylate (4.5 g, 22.5 mmol) in ethanol (20 ml). The resulting mixture was stirred at room temperature for 6 hours, then concentrated by evaporation to a volume of about 10 ml. This residue was shaked with diethyl ether and the aqueous layer was separated. This aqueous was acidified with 12N hydrochloric acid while the temperature was kept below 10° C. The resulting mixture was extracted with diethyl ether (3×50 ml). The combined extracts were dried over magnesium sulfate, filtered and evaporated to yield the desired product as a colorless oil.

Workup

  1. concentrationconcentrated by evaporation to a volume of about 10 ml
  2. customthe aqueous layer was separated
  3. customwas kept below 10° C
  4. extractionThe resulting mixture was extracted with diethyl ether (3×50 ml)
  5. dry with materialThe combined extracts were dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-2c2287b973a4429b876d73093bd3e712
Source dataset
uspto-grants-1988_08
Patent number
US04766145

Reaction notes

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