Sodium Hydroxide → 2-Oxatricyclo[3.3.1.13,7]decane-1-carboxylic acid

HRID 2198264Notes

Reaction equation

HRID 2198264 reaction equation
C[O:2][C:3]([C:5]12[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][CH:7]([CH2:8]3)[O:6]1)[CH2:12]2)=[O:4].[OH-].[Na+]>CO.O>[C:5]12([C:3]([OH:4])=[O:2])[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][CH:7]([CH2:8]3)[O:6]1)[CH2:12]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13617741HCID 13617741, compound

Product 1

HCID 668516802-Oxatricyclo[3.3.1.13,7]decane-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To a solution of 2-oxatricyclo-[3.3.1.13,7]decane-1-carboxylic acid methyl ester (Richard, Partch; William, Brewster; Bruce, Stokes; Croatia Chemical Acta (1969), 58(4), 661-669) (2.5 g, 12.6 mmol) in methanol/water (1:1, 100 mL) was added aqueous 5N NaOH solution (3.8 mL, 19 mmol). The mixture was stirred at room temperature for three hours and then extracted with methylene chloride to remove unreacted starting material. The aqueous layer was acidified (pH˜2) with 6N HCl and then extracted with methylene chloride. The combined organic extracts were dried (Na2SO4), filtered, and concentrated to provide the title compound. MS (ESI+) m/z 183 (M+H)+ . . . .

Workup

  1. extractionextracted with methylene chloride
  2. customto remove unreacted
  3. extractionextracted with methylene chloride
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-eaf53a6cbe784d5ba7ceb75025c792de
Source dataset
uspto-grants-2012_12
Patent number
US08338623B2

Reaction notes

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