2,6-Dichlorobenzaldehyde → 2,6-Dichloro-2',6'-dimethoxychalcone

HRID 990902

Reaction equation

HRID 990902 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[CH:4]=O.[CH3:11][C:12]([C:14]1[C:19]([O:20][CH3:21])=[CH:18][CH:17]=[CH:16][C:15]=1[O:22][CH3:23])=[O:13].[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:11][C:12]([C:14]1[C:15]([O:22][CH3:23])=[CH:16][CH:17]=[CH:18][C:19]=1[O:20][CH3:21])=[O:13]

Participants

6

Reactant 3

HCID 67372,6-DichlorobenzaldehydeHCID 14798Sodium HydroxideHCID 162671-(2,6-Dimethoxyphenyl)ethanone

Product 1

HCID 668658792,6-Dichloro-2',6'-dimethoxychalconeYield 51.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

(40) To a solution of 2,6-dichlorobenzaldehyde (485 mg, 2.77 mmol) and 2,6-dimethoxyacetophenone (500 mg, 2.77 mmol) in 4.1 ml of methanol was added 1.0 ml of 40% sodium hydroxide in water at 10° C. After stirring for 1.5 hours at room temperature, a solid appeared and was filtered. The precipitate was recrystallized from methanol to afford 481 mg (51.5%) of faint-yellow needles: mp 126.8-127.8° C. 1H NMR (250 MHz) δ 7.48-7.42 (d, 1H), 7.37-7.31 (m, 3H), 7.11-6.63-6.60 (d, 2H), 3.81 (s, 6H); 13C NMR (62.7 MHz) 195.1, 158.0, 138.4, 136.5, 135.2, 132.6, 131.4, 130.0, 129.0, 117.9, 104.2, 56.1 ppm. Elemental Analysis. Calculated for C17H14Cl2O3: C, 60.55; H, 4.19. Found: C, 60.60; H, 4.18.

Workup

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

Sources & evidence

ORD record
ord-b416a4dc77bf49cca72a36a9ade59ad1
Source dataset
uspto-grants-2002_10
Patent number
US06462075B1

Linked notes

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