Sodium Hydroxide → spiro[3.3]heptane-2,2-dicarboxylic acid

HRID 1049287Notes

Reaction equation

HRID 1049287 reaction equation
[CH2:1]1[C:4]2([CH2:7][CH2:6][CH2:5]2)[CH2:3][C:2]1([C:14]([O:16]C(C)C)=[O:15])[C:8]([O:10]C(C)C)=[O:9].[OH-].[Na+]>CO>[CH2:1]1[C:4]2([CH2:5][CH2:6][CH2:7]2)[CH2:3][C:2]1([C:14]([OH:16])=[O:15])[C:8]([OH:10])=[O:9]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 90403911HCID 90403911, compound

Product 1

HCID 271511spiro[3.3]heptane-2,2-dicarboxylic acidYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A solution of diisopropyl spiro[3.3]heptane-2,2-dicarboxylate (2.85 g, 10.62 mmol) in MeOH (20 mL) was treated with 2N NaOH (31.9 mL, 63.7 mmol) and heated at 50° C. overnight. The organics were removed under reduced pressure, the aqueous residue acidified with 3M HCl, cooled to 5° C. and the solid collected via filtration. The filtrate was extracted with DCM (2×), then EtOAc (2×) and the combined organics were dried over Na2SO4, concentrated to dryness and combined with the first solid to afford spiro[3.3]heptane-2,2-dicarboxylic acid (1.737 g, 89%). 1H NMR (400 MHz, DMSO-d6): δ 12.58 (s, 2H), 2.39 (s, 4H), 1.91 (t, J=7.5 Hz, 4H), 1.71 (m, 2H).

Workup

  1. customThe organics were removed under reduced pressure
  2. temperaturecooled to 5° C.
  3. filtrationthe solid collected via filtration
  4. extractionThe filtrate was extracted with DCM (2×)
  5. dry with materialEtOAc (2×) and the combined organics were dried over Na2SO4
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-2dcae4439f2945c4a6c204cba3268dfd
Source dataset
uspto-grants-2016_07
Patent number
US09382228B2

Reaction notes

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