Lithium hydroxide, monohydrate → Bicyclo[2.2.2]octane-1,4-dicarboxylic acid

HRID 1175827Notes

Reaction equation

HRID 1175827 reaction equation
[C:1]([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:3]C)=[O:2].O.[OH-].[Li+]>O1CCCC1.C(O)(C)C.O>[C:13]([C:8]12[CH2:11][CH2:12][C:5]([C:1]([OH:3])=[O:2])([CH2:10][CH2:9]1)[CH2:6][CH2:7]2)([OH:15])=[O:14]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 2802857dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate

Product 1

HCID 607709Bicyclo[2.2.2]octane-1,4-dicarboxylic acidYield 98%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 1,4-dicarbomethoxybicyclo[2.2.2]octane (31.7 g, 0.14 mole) in tetrahydrofuran (200 mL) and isopropanol (70 mL) was treated with a solution of lithium hydroxide hydrate (17.7 g, 0.42 mole) in water (200 mL), and the mixture was heated to 6°-70° C. for 2.5 h with stirring. The organic solvents were removed in vacuo, and the alkaline aqueous solution was filtered, then the filtrate was cooled on an ice bath and acidified with concentrated hydrochloric acid (40 mL). The solid was filtered, rinsed with cold water, and partially air dried overnight, then further dried under vacuum, triturated from acetonitrile, and redried in vacuo to afford 27.19 g (98%) of subject material as a white solid. No MS could be obtained. 1H NMR (d6-DMSO) δ 12.09 (br s, 2H), 1.66 (s, 12H).

Workup

  1. temperaturethe mixture was heated to 6°-70° C. for 2.5 h
  2. customThe organic solvents were removed in vacuo
  3. filtrationthe alkaline aqueous solution was filtered
  4. temperaturethe filtrate was cooled on an ice bath
  5. filtrationThe solid was filtered
  6. washrinsed with cold water, and partially air
  7. customdried overnight
  8. customfurther dried under vacuum
  9. customtriturated from acetonitrile
  10. customredried in vacuo

Sources & evidence

ORD record
ord-3a090af47c0249bab84a8b143d98df5c
Source dataset
uspto-grants-2010_11
Patent number
US07842707B2

Reaction notes

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