Hydrochloric Acid → Bicyclo(2.2.1)heptane-1,4-dicarboxylic acid

HRID 452995

Reaction equation

HRID 452995 reaction equation
[C:1]12([C:12]([O:14]C)=[O:13])[CH2:7][C:4]([C:8]([O:10]C)=[O:9])([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.[OH-].[K+].C(O)C.Cl>O>[C:1]12([C:12]([OH:14])=[O:13])[CH2:7][C:4]([C:8]([OH:10])=[O:9])([CH2:3][CH2:2]1)[CH2:5][CH2:6]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 13633974Dimethyl bicyclo[2.2.1]heptane-1,4-dicarboxylate

Product 1

HCID 14611213Bicyclo(2.2.1)heptane-1,4-dicarboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of Example 117A (3.18 g, 15.0 mmol), solid potassium hydroxide (8.4 g, 150 mmol), and a mixture of ethanol (75 mL) and water (15 mL) was heated at about 60° C. overnight. After cooling, the pH of the mixture was adjusted to about 1 by addition of 1N aqueous hydrochloric acid. The mixture was extracted with ethyl acetate (4×50 mL). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated by rotary evaporator to give a tan powder. The crude product was recrystallized from ethyl acetate/hexanes to give the title compound as a white solid that was used without further purification for the next step.

Workup

  1. temperatureAfter cooling
  2. extractionThe mixture was extracted with ethyl acetate (4×50 mL)
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporator
  6. customto give a tan powder
  7. customThe crude product was recrystallized from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-1d7df7b478144469bfe1d23644389d06
Source dataset
uspto-grants-2013_07
Patent number
US08492371B2

Linked notes

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