Lithium Hydroxide → HCID 18767672, compound

HRID 1408854Notes

Reaction equation

HRID 1408854 reaction equation
C[O:2][C:3]([C:5]12[CH2:12][C:9]([C:13]([O:15]C)=[O:14])([CH2:10][CH2:11]1)[CH2:8][CH2:7][CH2:6]2)=[O:4].[OH-].[Li+]>O1CCCC1.O>[C:9]12([C:13]([OH:15])=[O:14])[CH2:12][C:5]([C:3]([OH:4])=[O:2])([CH2:11][CH2:10]1)[CH2:6][CH2:7][CH2:8]2

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 13633976Dimethyl bicyclo[3.2.1]octane-1,5-dicarboxylate

Product 1

HCID 18767672HCID 18767672, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A solution of bicyclo[3.2.1]octane-1,5-dicarboxylic acid dimethyl ester (crude 3.01 g from step 2) in tetrahydrofuran (100 mL) was treated with 1 M of lithium hydroxide in water (75 mL) and warmed at 70° C. for 6 hours. The reaction was concentrated under reduced pressure and the resulting residue was partitioned between water and ethyl acetate. The aqueous layer was collected and washed again with ethyl acetate. The aqueous layer was acidified with 1N HCl to pH 2, and then extracted with ethyl acetate. The organic layer was collected, dried over anhydrous sodium sulfate, filtered, and evaporated to afford 725 mg of white solid, which was used in the next step without further purification.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customthe resulting residue was partitioned between water and ethyl acetate
  3. customThe aqueous layer was collected
  4. washwashed again with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. customThe organic layer was collected
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-818bc899fc184facbf9007cc5f5917a1
Source dataset
uspto-grants-2014_12
Patent number
US08921370B2

Reaction notes

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