Sodium Hydroxide → Spiro(2.5)octane-1-carboxylic Acid

HRID 2079461Notes

Reaction equation

HRID 2079461 reaction equation
[CH:1]1([C:9]([O:11]CC)=[O:10])[C:3]2([CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]2)[CH2:2]1.[OH-].[Na+]>O>[CH:1]1([C:9]([OH:11])=[O:10])[C:3]2([CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]2)[CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11206164Ethyl Spiro[2.5]octane-1-carboxylate

Product 1

HCID 10441897Spiro(2.5)octane-1-carboxylic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The product from Example 1A in 100 mL of water was treated with NaOH (11.4 g, 0.29 mol) and heated at reflux for 8 hours. The reaction mixture was allowed to cool to ambient temperature and extracted with diethyl ether (2×100 mL). The aqueous layer was acidified to pH 3 by careful addition of concentrated HCl and extracted with diethyl ether (3×100 mL). The ethereal extracts were combined and concentrated under reduced pressure to afford an oil that was distilled under vacuum (120° C., 60 torr) to provide the title compound as a clear oil. 1H NMR (CDCl3, 300 MHz) δ 11.95 (s, 1H), 1.30-1.60 (m, 11H), 1.13 (dd, 1H), 0.90 (dd, 1H); 13C NMR (CDCl3, 100 MHz) δ 179.6, 37.5, 32.1, 28.8, 26.0, 25.9, 25.6, 21.6; MS m/z 172 (M+NH4)+.

Workup

  1. temperatureheated
  2. temperatureat reflux for 8 hours
  3. extractionextracted with diethyl ether (2×100 mL)
  4. additionThe aqueous layer was acidified to pH 3 by careful addition of concentrated HCl
  5. extractionextracted with diethyl ether (3×100 mL)
  6. concentrationconcentrated under reduced pressure
  7. customto afford an oil that
  8. distillationwas distilled under vacuum (120° C., 60 torr)

Sources & evidence

ORD record
ord-4746c84dd16b412eae16ba0e10e555b1
Source dataset
uspto-grants-2011_04
Patent number
US07932245B2

Reaction notes

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