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

HRID 1693636Notes

Reaction equation

HRID 1693636 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 acidYield 83.6%

Reagents, catalysts & solvents 1

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

Procedure

To a solution of 2-oxa-tricyclo[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 5 N NaOH solution (3.8 mL, 19 mmol). The mixture was stirred at room temperature for 3 hours and then extracted with methylene chloride to remove unreacted starting material. The aqueous layer was acidified (pH2) with 6 N HCl and then extracted with methylene chloride. This organic extract was dried (Na2SO4), filtered and concentrated to provide 1.92 g of the title compound as white crystalline solid. MS (ESI+) m/z 183 (M+H)+.

Workup

  1. extractionextracted with methylene chloride
  2. customto remove unreacted
  3. extractionextracted with methylene chloride
  4. extractionThis organic extract
  5. dry with materialwas dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a79f78b50f8c450997f51fd187956405
Source dataset
uspto-grants-2012_04
Patent number
US08158663B2

Reaction notes

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