Acetic Anhydride → 7-Oxaspiro[3.5]nonane-6,8-dione
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]1Participants
3
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
- temperaturerefluxed overnight
- customAcetic anhydride was removed under reduced pressure
- customto give a brown oil, which
- customwas then recrystallized
- dissolutionby dissolving in ether/hexanes
- temperaturecooling to 0° C.
- customcollecting crystals
- filtrationby vacuum filtration
- 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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