2,4-Dichlorophenol → HCID 9279108, compound

HRID 1267812Notes

Reaction equation

HRID 1267812 reaction equation
[OH-].[K+].[Cl:3][C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[OH:11].Cl[C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][C:14]=1[N+:21]([O-:23])=[O:22]>>[Cl:3][C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[O:11][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][C:14]=1[N+:21]([O-:23])=[O:22]

Participants

4

Reactant 3

HCID 84492,4-DichlorophenolHCID 14797Potassium HydroxideHCID 855054-Chloro-3-nitrobenzaldehyde

Product 1

HCID 9279108HCID 9279108, compoundYield 80%

Procedure

To powdered potassium hydroxide (9.0 g, 0.12 mol) at 110° C. was added 2,4-dichlorophenol (19.0 g, 0.12 mol) in one portion. The mixture was stirred for 15 min. and a homogenous solution resulted. 4-Chloro-3-nitrobenzaldehyde (20.0 g, 0.11 mol) was added and the thick mixture was stirred at 110° C. for 1 h. After cooling to room temperature, the mixture was partitioned between 2M aqueous sodium hydroxide and ethyl acetate. The organic layer was separated, washed with brine and dried over magnesium sulfate. Evaporation of solvent and recrystallization from ethanol afforded 27.0 g (80%) of the title compound as a pale yellow solid. 1H NMR (CDCl3) δ9.80 (s, 1H), 8.48 (s, 1H), 7.90 (d, 1H), 7.53 (s, 1H), 7.35 (d, 1H), 7.16 (d, 1H), 6.88 (d, 1H). 3-Amino-4-(2,4-dichlorophenoxy)benzaldehyde

Workup

  1. customa homogenous solution resulted
  2. stirringthe thick mixture was stirred at 110° C. for 1 h
  3. customthe mixture was partitioned between 2M aqueous sodium hydroxide and ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. customEvaporation of solvent and recrystallization from ethanol

Sources & evidence

ORD record
ord-f7b65e8511af40b6b211871ef70ed779
Source dataset
uspto-grants-2003_04
Patent number
USRE038103E1

Reaction notes

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