Lithium hydroxide, monohydrate → HCID 68531723, compound

HRID 1808230Notes

Reaction equation

HRID 1808230 reaction equation
C[O:2][C:3]([CH:5]1[CH2:10][CH:9]2[CH2:11][CH2:12][CH:6]1[CH2:7][C:8]2=[O:13])=[O:4].O.[OH-].[Li+]>C1COCC1.CO.O.O>[O:13]=[C:8]1[CH2:7][CH:6]2[CH2:12][CH2:11][CH:9]1[CH2:10][CH:5]2[C:3]([OH:4])=[O:2]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 12273592HCID 12273592, compound

Product 1

HCID 68531723HCID 68531723, compoundYield 87.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

5-Oxo-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester (Preparation 73, 390 g, 2.14 mol, 1.0 eq) was taken up in a mixture of THF:MeOH:water (2:2:1, 2.0 L). A solution of lithiumhydroxide monohydrate (198 g, 4.71 mol, 2.2 eq) in water (1.0 L) was added dropwise while a dark green solution emerged. The temperature was kept below 30° C. by cooling with a waterbath. The reaction mixture was washed with DCM (2×500 mL). The combined organic layers were extracted with water (300 mL). The combined aqueous layers were brought to pH ˜1 with concentrated HCl solution and subsequently extracted with DCM (4×300 mL). The combined organic layers were dried over sodium sulfate and the solvent was removed under reduced pressure and stripped with toluene (2×). This furnished title compound as a brownish solid (314 g, 1.87 mol, 87%).

Workup

  1. customwas kept below 30° C.
  2. temperatureby cooling with a waterbath
  3. washThe reaction mixture was washed with DCM (2×500 mL)
  4. extractionThe combined organic layers were extracted with water (300 mL)
  5. extractionsubsequently extracted with DCM (4×300 mL)
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c0516e38714f413281c6b9e211a2fe22
Source dataset
uspto-grants-2013_01
Patent number
US08357711B2

Reaction notes

Loading…