Chromanone → Chroman

HRID 2064761Notes

Reaction equation

HRID 2064761 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. 1H-NMR (CDCl3): δ=2.04 (m, 2H); 2.82 (m, 2H); 4.21 (m, 2H); 6.80-6.89 (m, 2H); 7.04-7.14 (m, 2H).

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-8cf501e7387843d78b89c16614dbb494
Source dataset
uspto-grants-2012_10
Patent number
US08288435B2

Reaction notes

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