Benzaldehyde → 2,6-Bis(benzylidene)cyclohexanone

HRID 2113927Notes

Reaction equation

HRID 2113927 reaction equation
[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:8](=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[CH:8](=[C:2]1[CH2:3][CH2:4][CH2:5][C:6](=[CH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:1]1=[O:7])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 240BenzaldehydeHCID 7967Cyclohexanone

Product 1

HCID 953362,6-Bis(benzylidene)cyclohexanone

Procedure

(75) Cyclohexanone (10 mmol) and benzaldehyde (20 mmol) were used. The reaction stirred for 2 hours. A solid formed and was filtered. Recrystallization from ethanol yielded 2.01 g (73.4%) of bright-yellow flakes: mp 118.1-119.0° C. (lit. mp 116-117° C., Smith, et al., Can. J. Chem., 1973, 51, 1458-1470). 1H NMR (250 MHz) δ 7.83 (s, 2 H), 7.50-7.32 (m, 10 H), 2.95 (t, 4 H), 1.80 (p, 2 H); 13C NMR (62.7 MHz) 190.5, 137.1, 136.4, 136.1, 130.5, 128.8, 128.5, 28.6, 23.2 ppm.

Workup

  1. customA solid formed
  2. filtrationwas filtered
  3. customRecrystallization from ethanol
  4. customyielded 2.01 g (73.4%) of bright-yellow flakes

Sources & evidence

ORD record
ord-f021e52952d742f0acdcb12f1bbf118e
Source dataset
uspto-grants-2008_10
Patent number
US07432303B2

Reaction notes

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