Ethyl 2-(bicyclo[3.3.1]nonan-9-yl)acetate → 2-(Bicyclo[3.3.1]nonan-9-yl)acetic acid

HRID 1853432Notes

Reaction equation

HRID 1853432 reaction equation
[CH:1]12[CH:9]([CH2:10][C:11]([O:13]CC)=[O:12])[CH:5]([CH2:6][CH2:7][CH2:8]1)[CH2:4][CH2:3][CH2:2]2>CO.[OH-].[Na+]>[CH:5]12[CH:9]([CH2:10][C:11]([OH:13])=[O:12])[CH:1]([CH2:2][CH2:3][CH2:4]1)[CH2:8][CH2:7][CH2:6]2

Participants

4

Reactant 1

HCID 68773303Ethyl 2-(bicyclo[3.3.1]nonan-9-yl)acetate

Product 1

HCID 229236192-(Bicyclo[3.3.1]nonan-9-yl)acetic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of Example 56B (8.5 g 40.4 mmol) in methanol (100 mL), aqueous NaOH (50%, 25 mL) was added. The reaction was stirred at room temperature for 24 hours. Methanol was evaporated and the mixture was extracted with ether and then acidified with 6N HCl to pH 2. The mixture was extracted with ether (2×50 mL), the organic layer was dried with magnesium sulfate, filtered, and concentrated to afford the title compound.

Workup

  1. customMethanol was evaporated
  2. extractionthe mixture was extracted with ether
  3. extractionThe mixture was extracted with ether (2×50 mL)
  4. dry with materialthe organic layer was dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-72d914873ea8410ea1a4165b6d632424
Source dataset
uspto-grants-2015_02
Patent number
US08962639B2

Reaction notes

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