2,6-Dichlorobenzaldehyde → HCID 286708, compound

HRID 2113928Notes

Reaction equation

HRID 2113928 reaction equation
[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:8][C:9]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:10]=1[CH:11]=O>C(O)C>[Cl:8][C:9]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:10]=1[CH:11]=[C:2]1[CH2:3][CH2:4][CH2:5][C:6](=[CH:11][C:10]2[C:9]([Cl:8])=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:17])[C:1]1=[O:7]

Participants

4

Reactant 2

HCID 67372,6-DichlorobenzaldehydeHCID 7967Cyclohexanone

Product 1

HCID 286708HCID 286708, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(76) Cyclohexanone (10 mmol), 60 ml of ethanol, and 2,6-dichlorobenzaldehyde (20 mmol) were used. The reaction stirred for 4 hours. A solid formed and was filtered. Recrystallization from ethanol yielded 3.24 g (78.6%) of bright-yellow flakes: mp 185.0-186.0° C. (lit. mp 183° C., Smith et al., supra). 1H NMR (250 MHz) δ 7.60 (s, 2 H), 7.37-7.18 (m, 6 H), 2.45 (t, 4 H), 1.73 (p, 2 H); 13C NMR (62.7 MHz) 188.2, 140.3, 134.6, 134.4, 132.4, 129.6, 128.1, 28.4, 22.1 ppm.

Workup

  1. customA solid formed
  2. filtrationwas filtered
  3. customRecrystallization from ethanol
  4. customyielded 3.24 g (78.6%) of bright-yellow flakes

Sources & evidence

ORD record
ord-0fb67ad33e254f0e9c4730d316eb2945
Source dataset
uspto-grants-2008_10
Patent number
US07432303B2

Reaction notes

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