Chromanone → Chroman

HRID 560285Notes

Reaction equation

HRID 560285 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=O)[CH2:3][CH2:2]1>CC(O)=O.[Zn]>[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 68110Chromanone

Product 1

HCID 136319Chroman

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent2×

Conditions

Temperature
100 °C

Procedure

A solution of 4-chromanone (19.6 mmol) in HOAc (30 mL) is added to a suspension of zinc powder (445 mmol) in HOAc (60 mL). The mixture is stirred at 100° C. for 4 h, cooled to RT, filtered through celite and concentrated in vacuo. EtOAc and aq. NaOH solution (1.0 M) are added, the layers are separated and the aq. layer is extracted twice with EtOAc. The combined organic layers are dried over MgSO4 and concentrated in vacuo to give the desired product which is used without further purification.

Workup

  1. temperaturecooled to RT
  2. filtrationfiltered through celite and
  3. concentrationconcentrated in vacuo
  4. additionEtOAc and aq. NaOH solution (1.0 M) are added
  5. customthe layers are separated
  6. extractionthe aq. layer is extracted twice with EtOAc
  7. dry with materialThe combined organic layers are dried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-18581f12babf4edc873dc078513a43ba
Source dataset
uspto-grants-2011_11
Patent number
US08063099B2

Reaction notes

Loading…