Lithium hydroxide, monohydrate → 1,3-Dicarboxybicyclo[3.2.1]octane

HRID 1175829Notes

Reaction equation

HRID 1175829 reaction equation
[C:1]([C:5]12[CH2:12][CH:9]([CH2:10][CH2:11]1)[CH2:8][CH:7]([C:13]([O:15]C)=[O:14])[CH2:6]2)([O:3]C)=[O:2].O.[OH-].[Li+]>O1CCCC1.C(O)(C)C.O>[C:1]([C:5]12[CH2:12][CH:9]([CH2:10][CH2:11]1)[CH2:8][CH:7]([C:13]([OH:15])=[O:14])[CH2:6]2)([OH:3])=[O:2]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 684229871,3-Dicarbomethoxybicyclo[3.2.1]octane

Product 1

HCID 684249611,3-Dicarboxybicyclo[3.2.1]octaneYield 86.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 1,3-dicarbomethoxybicyclo[3.2.1]octane (8.26 g, 36.5 mmol) in tetrahydrofuran (50 mL) and isopropanol (16 mL) was treated with a solution of lithium hydroxide hydrate (4.20 g, 100 mmol) in water (50 mL), and the mixture was heated to 60°-70° C. for 2 h with stirring. The organic solvents were removed in vacuo, and the alkaline aqueous solution was cooled on an ice bath and acidified with concentrated hydrochloric acid (10 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 6.25 g (86%) of subject material as a white solid. No MS could be obtained. 1H NMR (CDCl3+drop d6-DMSO) δ 2.15-2.25 (m, 1H), 1.95-2.05 (m, 2H), 1.40-1.70 (m, 9H).

Workup

  1. temperaturethe mixture was heated to 60°-70° C. for 2 h
  2. customThe organic solvents were removed in vacuo
  3. temperaturethe alkaline aqueous solution was cooled on an ice bath
  4. filtrationThe solid was filtered
  5. washrinsed with cold water, and partially air
  6. customdried overnight
  7. customfurther dried under vacuum
  8. customtriturated from acetonitrile
  9. customredried in vacuo

Sources & evidence

ORD record
ord-88678b9f8592420c8511ba65c6cddb25
Source dataset
uspto-grants-2010_11
Patent number
US07842707B2

Reaction notes

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