Lithium hydroxide, monohydrate → HCID 68423555, compound

HRID 1175832Notes

Reaction equation

HRID 1175832 reaction equation
[C:1]([C:5]12[CH2:11][CH:9]([CH2:10]1)[CH2:8][CH:7]([C:12]([O:14]C)=[O:13])[CH2:6]2)([O:3]C)=[O:2].O.[OH-].[Li+]>O1CCCC1.C(O)(C)C.O>[C:1]([C:5]12[CH2:11][CH:9]([CH2:10]1)[CH2:8][CH:7]([C:12]([OH:14])=[O:13])[CH2:6]2)([OH:3])=[O:2]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68424862HCID 68424862, compound

Product 1

HCID 68423555HCID 68423555, compoundYield 379.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 1,3-dicarbomethoxybicyclo[3.1.1]heptane (1.90 g, 8.95 mmol) in tetrahydrofuran (25 mL) and isopropanol (8 mL) was treated with a solution of lithium hydroxide hydrate (2.1 g, 50 mmol) in water (25 mL), and the mixture was heated to 60°-70° C. for 3 h with stirring. The organic solvents were removed in vacuo, and the alkaline aqueous solution was cooled on an ice bath and acidified with 6N hydrochloric acid (10 mL). The solid was filtered, rinsed with cold water, and partially air dried overnight, then further dried under vacuum to afford 6.25 g (86%) of subject material as a white solid. No MS could be obtained. 1H NMR (CDCl3) δ 2.40-2.50 (m, 2H), 1.90-2.00 (m, 4H), 1.80-1.90 (m, 2H), 1.70-1.80 (m, 2H).

Workup

  1. temperaturethe mixture was heated to 60°-70° C. for 3 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

Sources & evidence

ORD record
ord-3975ef111fd6497282e2186324d4c034
Source dataset
uspto-grants-2010_11
Patent number
US07842707B2

Reaction notes

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