4-Methoxybenzaldehyde → Cinnamoylbenzene

HRID 1095268Notes

Reaction equation

HRID 1095268 reaction equation
O[C:2]1[C:7]([C:8](=[O:10])[CH3:9])=[C:6](OC)[C:5](OC)=[C:4](OC)[CH:3]=1.CO[C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1.CC([O-])(C)C.[K+]>C(O)C>[C:22]1([CH:23]=[CH:9][C:8]([C:7]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[O:10])[CH:25]=[CH:26][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 312444-MethoxybenzaldehydeHCID 98993751-(6-Hydroxy-2,3,4-trimethoxyphenyl)ethan-1-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 7189CinnamoylbenzeneYield 143.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-(6-hydroxy-2,3,4,-Trimethoxyphenyl)ethanone 5 (2.26 g, 10 mmol), 4-methoxybenzaldehyde (1.63 g, 12 mmol) and t-BuOK (2.11 g, 22 mmol) in ethanol (30 mL) was refluxed for 4 h. The reaction mixture was poured onto crushed ice (100 g). The resulting precipitate was filtered and washed with water. The residue was air-dried at room temperature. The crude product was recrystallized from ethyl acetate to afford chalcone as orange crystals (2.99 g, 87%): 1H NMR (CDCl3, 200 M Hz) δ 11.75 (br s, 1H), 7.84 (s, 2H), 7.60 (d, J=8.8 Hz, 2H), 6.93 (d, J=8.8 Hz, 2H), 6.29 (s 1H), 3.93 (s 3H), 3.90 (s, 3 M), 3.85 (s, 3H), 3.84 (s, 3H); 13C NMR (CDCl3, 50 M Hz) δ 192.7 (s), 162.6 (s), 161.5 (s), 159.9 (s), 154.9 (s), 143.3 (d), 135.2 (s), 130.1 (d, 2C), 128.0 (s), 124.0 (d), 114.4 (d, 2C), 108.7 (s), 96.5 (d), 61.8 (q), 61.2 (q), 56.0 (q), 55.3 (q).

Workup

  1. additionThe reaction mixture was poured
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water
  4. customThe residue was air-dried at room temperature
  5. customThe crude product was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-403292ab4a9d47f28b32fe146c678314
Source dataset
uspto-grants-2012_03
Patent number
US08138165B2

Reaction notes

Loading…