Lithium Hydroxide → HCID 18628853, compound

HRID 1060732Notes

Reaction equation

HRID 1060732 reaction equation
[CH:1]1([CH2:7][CH:8]([C:14]([O:16]CC)=[O:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Li+]>C(O)C.O>[CH:1]1([CH2:7][CH:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:14]([OH:16])=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 599487diethyl 2-cyclohexylmethylmalonate

Product 1

HCID 18628853HCID 18628853, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution comprised of diethyl 2-cyclohexylmethylmalonate (12.817 g, 50 mmol) in ethanol (100 mL) was treated with a solution of comprised of lithium hydroxide (1.198 g, 50 mmol) in water (50 mL) and the mixture was stirred for approximately 12 hours at ambient temperature. Solvent was removed by evaporation and the residue was diluted with water (50 mL). The dilution was extracted with diethyl ether (2×). The aqueous layer was cooled to 0° C., acidified to pH 1.5 with 1N hydrochloric acid (50 mL), saturated with solid sodium chloride and then extracted with ethyl acetate (2×). The combined ethyl acetate extracts were dried (MgSO4) and concentrated. The residue was dried to provide 3-cyclohexyl-2-ethoxycarbonylpropionic acid (8.52 g, 37 mmol) as an oil.

Workup

  1. additionwas treated with a solution
  2. customSolvent was removed by evaporation
  3. additionthe residue was diluted with water (50 mL)
  4. extractionThe dilution was extracted with diethyl ether (2×)
  5. temperatureThe aqueous layer was cooled to 0° C.
  6. extractionextracted with ethyl acetate (2×)
  7. dry with materialThe combined ethyl acetate extracts were dried (MgSO4)
  8. concentrationconcentrated
  9. customThe residue was dried

Sources & evidence

ORD record
ord-becbf32b2d8c4bc9abc5bc8a5b2471ba
Source dataset
uspto-grants-2003_02
Patent number
US06525036B2

Reaction notes

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