dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate → 4-(Methoxycarbonyl)bicyclo[2.2.2]octane-1-carboxylic acid

HRID 480157Notes

Reaction equation

HRID 480157 reaction equation
[CH3:1][O:2][C:3]([C:5]12[CH2:12][CH2:11][C:8]([C:13]([O:15]C)=[O:14])([CH2:9][CH2:10]1)[CH2:7][CH2:6]2)=[O:4].O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-]>CO.O>[CH3:1][O:2][C:3]([C:5]12[CH2:12][CH2:11][C:8]([C:13]([OH:15])=[O:14])([CH2:9][CH2:10]1)[CH2:7][CH2:6]2)=[O:4]

Participants

5

Reactant 2

HCID 2802857dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylateHCID 17749109Barium hydroxide, octahydrate

Product 1

HCID 110420624-(Methoxycarbonyl)bicyclo[2.2.2]octane-1-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
22.5 °C

Procedure

A mixture of Bicyclo[2.2.2]octane-1,4-dicarboxylic acid dimethyl ester (III, Example 80, 20.4 g, 89.5 mmol), barium hydroxide octahydrate (14 g, 44.7 mmol) in methanol (160 ml) and water (40 ml) is stirred at 20-25° C. for 18 hour. The mixture is diluted with water (600 ml) and extracted with hexane (150 ml×2). The aqueous mixture is acidified (6 N hydrochloric acid) to pH=1-2 and extracted with chloroform (150 ml×2). The combined chloroform extracts are concentrated. The residue is dissolved in toluene, filtered and concentrated to give the title compound, mp=169-173° C.

Workup

  1. extractionextracted with hexane (150 ml×2)
  2. extractionextracted with chloroform (150 ml×2)
  3. concentrationThe combined chloroform extracts are concentrated
  4. dissolutionThe residue is dissolved in toluene
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5961e5fba2634cb0ba23abad98264fb8
Source dataset
uspto-grants-2003_11
Patent number
US06649600B1

Reaction notes

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