2,6-Dichlorobenzaldehyde → HCID 66865602, compound

HRID 990899Notes

Reaction equation

HRID 990899 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, 7H), 7.10-7.03 (d, 1H); 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-45b61b20b2b34086b37008e2dc437717
Source dataset
uspto-grants-2002_10
Patent number
US06462075B1

Reaction notes

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