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

HRID 920769Notes

Reaction equation

HRID 920769 reaction equation
[CH3:1][C:2]1([CH3:18])[CH2:5][C:4]([C:12]([O:14]C(C)C)=[O:13])([C:6]([O:8]C(C)C)=[O:7])[CH2:3]1.[OH-].[K+]>C(O)C.O>[CH3:1][C:2]1([CH3:18])[CH2:5][C:4]([C:6]([OH:8])=[O:7])([C:12]([OH:14])=[O:13])[CH2:3]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 118062240Diisopropyl 3,3-dimethylcyclobutane-1,1-dicarboxylate

Product 1

HCID 147897663,3-Dimethylcyclobutane-1,1-dicarboxylic acidYield 89.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of Intermediate 285B (1.5 g, 5.85 mmol) in ethanol (20 ml) was added a solution of KOH (1.313 g, 23.41 mmol) in water (10 mL). The resulting solution was stirred at 80° C. for 16 h. The reaction mixture was cooled to RT, quenched with crushed ice and extracted with diethyl ether (2×50 mL). The combined organic layers were dried over Na2SO4 and evaporated to afford Intermediate 285C as a viscous liquid (0.9 g, 89% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.64 (br. s., 2H), 2.17-2.29 (m, 4H), 1.01-1.12 (m, 6H).

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. customquenched with crushed ice
  3. extractionextracted with diethyl ether (2×50 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-de265ff341e94d0d9bf493f0a94f8b81
Source dataset
uspto-grants-2016_03
Patent number
US09273058B2

Reaction notes

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