Barium hydroxide, octahydrate → HCID 25257891, compound

HRID 2353079Notes

Reaction equation

HRID 2353079 reaction equation
[C:1]12([C:14]([O:16]C)=[O:15])[CH2:9][CH2:8][C:5]([C:10]([O:12][CH3:13])=[O:11])([CH2:6][CH2:7]1)[CH2:4][CH2:3][CH2:2]2.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-]>CO.O>[CH3:13][O:12][C:10]([C:5]12[CH2:6][CH2:7][C:1]([C:14]([OH:16])=[O:15])([CH2:9][CH2:8]1)[CH2:2][CH2:3][CH2:4]2)=[O:11]

Participants

5

Reactant 2

HCID 17749109Barium hydroxide, octahydrateHCID 67413550HCID 67413550, compound

Product 1

HCID 25257891HCID 25257891, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a stirred solution of dimethyl bicyclo[3.2.2]nonane-1,5-dicarboxylate (2.02 g, 8.41 mmol), in methanol (20 mL) and water (4 mL) was added barium hydroxide octahydrate (1.33 g, 4.20 mmol). The reaction mixture was stirred vigorously at ambient temperature overnight. The reaction mixture was stirred vigorously at ambient temperature overnight. The reaction mixture was diluted with water (20 mL) and washed with isohexane (2×100 mL), then the aqueous phase was acidified with 2M HC1 to pH 2 and extracted into EtOAc (2×100 mL). The organic extracts were combined, dried (MgSO4) and concentrated to leave the title compound (931 mg, 4.11 mmol, 49%) as a clear colourless gum which slowly formed a white solid; 1H NMR (CDCl3) δ 1.72-1.75 (m, 2H), 1.87-1.92 (m, 12H), 3.65 (s, 3H); GC-MS EI m/e M+ 226.

Workup

  1. stirringThe reaction mixture was stirred vigorously at ambient temperature overnight
  2. washwashed with isohexane (2×100 mL)
  3. extractionto pH 2 and extracted into EtOAc (2×100 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f4976bba3ba64485b70b51606233e9fc
Source dataset
uspto-grants-2010_07
Patent number
US07749997B2

Reaction notes

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