Hydrochloric Acid → 2-Oxatricyclo[3.3.1.13,7]decane-1-carboxylic acid

HRID 1853429Notes

Reaction equation

HRID 1853429 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+].Cl>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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 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 54A (2.5 g, 12.6 mmol) in methanol/water (1:1, 100 mL), 5 N aqueous NaOH (3.8 mL, 19 mmol) was added. The mixture was stirred at room temperature for 3 hours and then extracted with dichloromethane to remove un-reacted starting material. The aqueous layer was acidified (pH˜2) with 6 N aqueous HCl and then extracted with dichloromethane. The combined acidic extracts were dried (Na2SO4), filtered, and concentrated under reduced pressure to afford 1.92 g of the title compound. MS (ESI+) m/z 183 (M+H)+

Workup

  1. extractionextracted with dichloromethane
  2. customto remove
  3. customun-reacted
  4. extractionextracted with dichloromethane
  5. dry with materialThe combined acidic extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b7116422d2cf42b1885b62839838970d
Source dataset
uspto-grants-2015_02
Patent number
US08962639B2

Reaction notes

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