2,6-Dichlorobenzaldehyde → HCID 317159, compound

HRID 2113931Notes

Reaction equation

HRID 2113931 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[CH:4]=O.[C:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:13])[CH3:12].[OH-].[Na+]>CO.O>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[CH:4]=[CH:12][C:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:13]

Participants

6

Reactant 3

HCID 67372,6-DichlorobenzaldehydeHCID 7410AcetophenoneHCID 14798Sodium Hydroxide

Product 1

HCID 317159HCID 317159, compoundYield 60.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

(31) (Canadian Journal of Chemistry. 1968 46, 1952-6). To a solution of 2,6-dichlorobenzaldehyde (1.75 g, 10.0 mmol) and acetophenone (1.20 g, 10.0 mmol) in 30.0 ml of methanol was added 4.4 ml of 40% sodium hydroxide in water at 10° C. After stirring for 3 hours at room temperature, a solid appeared and was filtered. The precipitate was recrystallized from methanol to afford 1.68 g (60.6%) of yellow needles: mp 84.5-85.3° C. (lit. mp 83° C. Kuck and Grutzmacher, Org. Mass. Spect. 1978, 13, 90-102). 1H NMR (250 MHz) δ 8.05-8.01 (m, 2 H), 7.90-7.84 (d, 1 H), 7.70-7.64 (d, 1 H), 7.62-7.48 (m, 3 H), 7.41-7.37 (d, 2 H), 7.24-7.18 (dd, 1 H); 13C NMR (62.7 MHz) 190.3, 139.0, 135.3, 133.3 132.8, 130.7, 130.0, 129.0, 128.9 ppm.

Workup

  1. filtrationwas filtered
  2. customThe precipitate was recrystallized from methanol

Sources & evidence

ORD record
ord-39a98b59fc6f46efb711e94c78b2b657
Source dataset
uspto-grants-2008_10
Patent number
US07432303B2

Reaction notes

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