2,6-Dichlorobenzaldehyde → HCID 66865602, compound

HRID 1071769Notes

Reaction equation

HRID 1071769 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[CH:4]=[O:5].[CH3:11][C:12]([C:14]1[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:21])=O.[OH-].[Na+]>C(O)C.O>[Cl:20][C:19]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:21])[C:14]=1[CH:12]=[CH:11][C:4]([C:3]1[C:2]([Cl:1])=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:10])=[O:5]

Participants

6

Reactant 3

HCID 67372,6-DichlorobenzaldehydeHCID 14798Sodium HydroxideHCID 748771-(2,6-Dichlorophenyl)ethan-1-one

Product 1

HCID 66865602HCID 66865602, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

(32) To a solution of the 2,6-dichlorobenzaldehyde (438 mg, 2.50 mmol) and 2,6-dichloroacetophenone (473 mg, 2.50 mmol) in 3.7 ml of ethanol was added 0.1 ml of 40% sodium hydroxide in water at 10° C. After stirring for 2 hours at room temperature, a solid appeared and was filtered. The precipitate was recrystallized from methanol to afford 465 mg (53.8%) of white, cottony needles: mp 130-130.4° C. (lit. mp 124-125° C., Kaiser, et al., Monatshefte fur Chemie, 1997, 128, 1247-1254). 1H NMR (250 MHz) δ 7.43-7.17 (m, 7 H), 7.10-7.03 (d, 1 H); 13C NMR (62.7 MHz) 193.0, 141.7, 137.5, 135.3 134.4, 132.1, 131.8, 131.0, 130.6, 129.0, 128.3 ppm.

Workup

  1. filtrationwas filtered
  2. customThe precipitate was recrystallized from methanol
  3. customto afford 465 mg (53.8%) of white, cottony needles

Sources & evidence

ORD record
ord-d2d867909c054f2282bf24d73abfde7d
Source dataset
uspto-grants-2005_06
Patent number
US06906105B2

Reaction notes

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