Acetophenone → Cinnamoylbenzene

HRID 11759

Reaction equation

HRID 11759 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=O)[CH3:2].[CH3:10][O-:11].[Na+]>C1COCC1.CO>[C:4]1([CH:1]=[CH:2][C:10]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[O:11])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 7410AcetophenoneHCID 10942334Sodium Methoxide

Product 1

HCID 7189Cinnamoylbenzene

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Reaction of Aldehydes with Wang Resin-bound Acetophenones: Each packet of Acetophenone-Wang resin was transferred to a 250 mL PP bottle, to which a solution of NaOMe (51.2 mmol, 20 eq, 0.25 M) in 50% THF-MeOH (205 mL) and an aldehyde (51.2 mmol, 20 eq, 0.25 M) were added sequentially. After shaking at room temperature for 3 days, the packet was washed several times with MeOH (3×80 mL) and alternatively with DMF (80 mL) and MeOH (80 mL) for 3 cycles, followed by washes of DCM (2×80 mL) and MeOH (3×80 mL). The packet was air-dried overnight to afford a resin-bound Chalcone, that varied in color from yellow to dark red depending on the aldehyde used.

Workup

  1. washthe packet was washed several times with MeOH (3×80 mL)
  2. customThe packet was air-dried overnight

Sources & evidence

ORD record
ord-91a500af0c324fcda1988389295dd3f8
Source dataset
uspto-grants-2006_08
Patent number
US07098336B2

Linked notes

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