Potassium Hydroxide → HCID 18405668, compound

HRID 653964Notes

Reaction equation

HRID 653964 reaction equation
C([O:3][C:4](=[O:17])[CH2:5][CH2:6][CH:7]1[CH:14]2[CH2:15][CH:10]3[CH2:11][CH:12]([CH2:16][CH:8]1[CH2:9]3)[CH2:13]2)C.[OH-].[K+]>C(O)C>[CH:14]12[CH2:15][CH:10]3[CH2:11][CH:12]([CH2:16][CH:8]([CH2:9]3)[CH:7]1[CH2:6][CH2:5][C:4]([OH:17])=[O:3])[CH2:13]2

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 53933676Ethyl tricyclo[3.3.1.13,7]decane-2-propanoate

Product 1

HCID 18405668HCID 18405668, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of tricyclo[3.3.1.1-3,7]decane-2-propanoic acid ethyl ester (0.011 mol, 2.68 g) in anhydrous ethanol (135 mL) was added potassium hydroxide (0.057 mol, 3.18 g) in several portions. The clear solution was heated at reflux for 1 h, cooled to ambient temperature, and concentrated. The yellow residue was partitioned with CH2Cl2 (100 mL) and water (50 mL), and the basic, aqueous phase extracted with CH2Cl2 (100 mL). The aqueous phase was re-acidified (pH 2) by the addition of 10% aqueous hydrochloric acid, and extracted with CH2Cl2 (3×50 mL). The combined organic extracts were dried (Na2SO4) and concentrated to provide tricyclo[3.3.1.1-3,7]decane-2-propanoic acid as a white solid (96%, 2.27 g). mp 115.5°-116° C.

Workup

  1. temperatureThe clear solution was heated
  2. temperatureat reflux for 1 h
  3. concentrationconcentrated
  4. customThe yellow residue was partitioned with CH2Cl2 (100 mL) and water (50 mL)
  5. extractionthe basic, aqueous phase extracted with CH2Cl2 (100 mL)
  6. additionby the addition of 10% aqueous hydrochloric acid
  7. extractionextracted with CH2Cl2 (3×50 mL)
  8. dry with materialThe combined organic extracts were dried (Na2SO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-828630fc34d44e92bbcf13244ec092bf
Source dataset
uspto-grants-1992_07
Patent number
US05128448

Reaction notes

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