Water → 1-Isopropyl-3-oxocyclopentanecarboxylic acid

HRID 1816961Notes

Reaction equation

HRID 1816961 reaction equation
[CH:1]([C:4]1([C:13]([O:15]C(C)(C)C)=[O:14])[CH2:8][CH2:7][C:6](OC)([O:9]C)[CH2:5]1)([CH3:3])[CH3:2].O>Cl.O1CCOCC1>[CH:1]([C:4]1([C:13]([OH:15])=[O:14])[CH2:8][CH2:7][C:6](=[O:9])[CH2:5]1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 962WaterHCID 58987981Tert-butyl 1-isopropyl-3,3-dimethoxycyclopentanecarboxylate

Product 1

HCID 186143931-Isopropyl-3-oxocyclopentanecarboxylic acidYield 104.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl 1-isopropyl-3,3-dimethoxycyclopentanecarboxylate (8.32 g, 30.5 mmol) was dissolved in 4 N anhydrous HCl in dioxane (50 mL) and water (10 mL) was added. The reaction mixture was stirred at room temperature overnight, then was concentrated. The residue was dissolved in DCM, dried over anhydrous MgSO4, filtered, and concentrated to give 5.44 g of 1-isopropyl-3-oxocyclopentanecarboxylic acid (used without purification).

Workup

  1. concentrationwas concentrated
  2. dissolutionThe residue was dissolved in DCM
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-945d3f3d6fe44dc4a7102398e94ecf06
Source dataset
uspto-grants-2009_10
Patent number
US07598243B2

Reaction notes

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