Acetic Anhydride → 7-Oxaspiro[3.5]nonane-6,8-dione

HRID 925296Notes

Reaction equation

HRID 925296 reaction equation
[C:1]1([CH2:9][C:10]([OH:12])=[O:11])([CH2:5][C:6]([OH:8])=O)[CH2:4][CH2:3][CH2:2]1.C(OC(=O)C)(=O)C>>[CH2:2]1[C:1]2([CH2:5][C:6](=[O:8])[O:12][C:10](=[O:11])[CH2:9]2)[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 187043182,2'-(Cyclobutane-1,1-diyl)diacetic acid

Product 1

HCID 534387167-Oxaspiro[3.5]nonane-6,8-dioneYield 52.8%

Procedure

2,2′-(cyclobutane-1,1-diyl)diacetic acid (0.7 g, 4.07 mmol) was dissolved in acetic anhydride (5.75 mL, 61.0 mmol) and refluxed overnight. The solution was cooled to r.t. Acetic anhydride was removed under reduced pressure to give a brown oil, which was then recrystallized by dissolving in ether/hexanes, cooling to 0° C. and collecting crystals by vacuum filtration. The crystals were dried under vacuum overnight producing 7-oxaspiro[3.5]nonane-6,8-dione (2.147 mmol, 52.8% yield) as a light brown solid.

Workup

  1. temperaturerefluxed overnight
  2. customAcetic anhydride was removed under reduced pressure
  3. customto give a brown oil, which
  4. customwas then recrystallized
  5. dissolutionby dissolving in ether/hexanes
  6. temperaturecooling to 0° C.
  7. customcollecting crystals
  8. filtrationby vacuum filtration
  9. customThe crystals were dried under vacuum overnight

Sources & evidence

ORD record
ord-e96fc88d5b2b4d42afd7444b499dc313
Source dataset
uspto-grants-2016_03
Patent number
US09284283B2

Reaction notes

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