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

HRID 538800Notes

Reaction equation

HRID 538800 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 Example 81A (2.5 g, 12.6 mmol) in methanol/water (1:1, 100 mL) was added 5 N aqueous NaOH (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 (pH˜2) with 6 N aqueous HCl and then extracted with methylene chloride. The combined acidic extracts were dried (Na2SO4), filtered and concentrated to afford 1.92 g of 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 acidic extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f56df99327064888aeaee2893f646b29
Source dataset
uspto-grants-2014_10
Patent number
US08865753B2

Reaction notes

Loading…