Methanol → HCID 18614386, compound

HRID 1725755Notes

Reaction equation

HRID 1725755 reaction equation
[CH2:1]=[C:2]1[CH2:6][CH2:5][C:4]([CH:11]([CH3:13])[CH3:12])([C:7]([O:9]C)=[O:8])[CH2:3]1.O.[OH-].[Li+].CO>O1CCOCC1.O>[CH2:1]=[C:2]1[CH2:6][CH2:5][C:4]([CH:11]([CH3:13])[CH3:12])([C:7]([OH:9])=[O:8])[CH2:3]1

Participants

6

Reactant 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 18614378HCID 18614378, compound

Product 1

HCID 18614386HCID 18614386, compoundYield 111.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of the methyl 3-methylene-1-isopropylcyclopentanecarboxylate (Step A, 1.21 g, 6.64 mmol) in a mixture of dioxane (4 mL) and water (4 mL) containing 1.114 g (26.56 mmol) of lithium hydroxide monohydrate was homogenized with methanol, and stirred at 80° C. for 48 hrs. The solvent was removed in vacuo, the residue was dissolved in water and the non-acidic components were extracted with diethyl ether (3×30 mL), combined ethers were back-washed with water (1×30 mL). The combined aqueous phases were acidified with 2N HCl and extracted with chloroform (6×30 mL), dried (anhydrous magnesium sulfate) and evaporated to dryness to leave 1.25 g of crude acid. It was used in the next reaction step without any further purification.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in water
  3. extractionthe non-acidic components were extracted with diethyl ether (3×30 mL)
  4. washwere back-washed with water (1×30 mL)
  5. extractionextracted with chloroform (6×30 mL)
  6. dry with materialdried (anhydrous magnesium sulfate)
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-13ad3a811faf4546bc435ea116070bbc
Source dataset
uspto-grants-2009_02
Patent number
US07491737B2

Reaction notes

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