(+-)-2-Butanol → Chromanone

HRID 714603Notes

Reaction equation

HRID 714603 reaction equation
I[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.N1CCCCC1.C1CCN2C(=NCCC2)CC1.[CH:27]([OH:31])(CC)[CH3:28]>>[CH:3]1[CH:2]=[CH:9][C:8]2[O:31][CH2:27][CH2:28][C:6](=[O:7])[C:5]=2[CH:4]=1

Participants

5

Reactant 4

HCID 6568(+-)-2-ButanolHCID 8082PiperidineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 966574-Iodobenzaldehyde

Product 1

HCID 68110Chromanone

Conditions

Temperature
90 °C

Procedure

A solution of protected hydroxyarylketone (1.0 equiv), 4-iodobenzaldehyde (1.0 equiv), piperidine (0.35 equiv), and DBU (0.35 equiv) in s-butanol (1.0 M) was heated at reflux. Using a Dean-Stark trap, half of the solvent was removed over 30-40 min, and the reaction was kept at reflux without further concentration for additional 4-8 h. The reaction mixture was cooled to 90° C., i-propanol (0.7-1.0 fold of s-butanol v/v) was added, and the reaction was allowed to cool to room temperature. Any large pieces of material were broken down with a spatula, and the suspension was stirred overnight (Note #1 & 2). The precipitate was collected by filtration to give the corresponding chromanone.

Workup

  1. temperatureat reflux
  2. customwas removed over 30-40 min
  3. temperatureat reflux without further concentration for additional 4-8 h
  4. additioni-propanol (0.7-1.0 fold of s-butanol v/v) was added
  5. temperatureto cool to room temperature
  6. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-9f2ea4deef9a4a8f82de8fdbc394dc8b
Source dataset
uspto-grants-2015_11
Patent number
US09187460B2

Reaction notes

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