Sodium Hydroxide → 862501-94-8

HRID 555677Notes

Reaction equation

HRID 555677 reaction equation
[C:1]12([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8][CH2:7][C:4]([C:9]([O:11]C)=[O:10])([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.[OH-].[Na+]>CO>[C:1]12([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:2][CH2:3][C:4]([C:9]([OH:11])=[O:10])([CH2:5][CH2:6]1)[CH2:7][CH2:8]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 23149682HCID 23149682, compound

Product 1

HCID 23149699862501-94-8Yield 73.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1,1-Dimethylethyl methyl bicyclo[2.2.2]octane-1,4-dicarboxylate (495 mg) was dissolved in methanol (5 mL). To this solution, a 2 mol/L aqueous sodium hydroxide solution (0.92 mL) was added and the mixture was stirred at room temperature for 8 hours and then at 50° C. for 2 hours. Methanol in the mixture was evaporated under reduced pressure. Water was added to the resulting residue and the mixture was washed with diethyl ether and was neutralized with 3 mol/L hydrochloric acid. The resulting crystals were filtered, washed with water, and dried under reduced pressure to give 1,1-dimethylethyl hydrogen bicyclo[2.2.2]octane-1,4-dicarboxylate (344 mg).

Workup

  1. waitat 50° C. for 2 hours
  2. customMethanol in the mixture was evaporated under reduced pressure
  3. additionWater was added to the resulting residue
  4. washthe mixture was washed with diethyl ether
  5. filtrationThe resulting crystals were filtered
  6. washwashed with water
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-4f4ac773b7d6430ab5c48f6e88e3463a
Source dataset
uspto-grants-2011_11
Patent number
US08053465B2

Reaction notes

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