Lithium hydroxide, monohydrate → HCID 67001993, compound

HRID 2191590Notes

Reaction equation

HRID 2191590 reaction equation
C[O:2][C:3]([C:5]1([C:10]([CH:12]2[CH2:14][CH2:13]2)=[O:11])[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].O[Li].O>CCO.O>[CH:12]1([C:10]([C:5]2([C:3]([OH:4])=[O:2])[CH2:6][CH2:7][CH2:8][CH2:9]2)=[O:11])[CH2:14][CH2:13]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 58525273HCID 58525273, compound

Product 1

HCID 67001993HCID 67001993, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of 1-cyclopropanecarbonyl-cyclopentane carboxylic acid methyl ester (0.62 g, 3.1 mmol) in EtOH (10 mL) were added LiOH.H2O (0.53 g, 12.6 mmol) and water (3 mL). The reaction mixture was stirred at room temperature overnight then diluted with water and washed with Et2O. The aqueous layer was acidified with conc. HCl to pH=2 then extracted with Et2O (2×). The combined second organic extracts were dried over Na2SO4 and concentrated to afford 0.36 g (64%) of 1-cyclopropanecarbonyl-cyclopentane carboxylic acid as a pale yellow oil.

Workup

  1. washwashed with Et2O
  2. extractionthen extracted with Et2O (2×)
  3. dry with materialThe combined second organic extracts were dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7cdc7d57d86944bc85a69f38188e82aa
Source dataset
uspto-grants-2012_12
Patent number
US08329699B2

Reaction notes

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