Hydrochloric Acid → (E)-3-[4-(benzyloxy)-3-nitrophenyl]-1-(2-hydroxy-5-methyl-3-nitrophenyl)-2-propen-1-one

HRID 1841357Notes

Reaction equation

HRID 1841357 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:10])=[O:9])[C:5]([OH:11])=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1.[CH2:15]([O:22][C:23]1[CH:30]=[CH:29][C:26]([CH:27]=O)=[CH:25][C:24]=1[N+:31]([O-:33])=[O:32])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[OH-].[Na+].Cl>O.C(O)C>[CH2:15]([O:22][C:23]1[CH:30]=[CH:29][C:26](/[CH:27]=[CH:10]/[C:8]([C:6]2[CH:7]=[C:2]([CH3:1])[CH:3]=[C:4]([N+:12]([O-:14])=[O:13])[C:5]=2[OH:11])=[O:9])=[CH:25][C:24]=1[N+:31]([O-:33])=[O:32])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 7361622'-Hydroxy-5'-methyl-3'-nitroacetophenoneHCID 70235544-(Benzyloxy)-3-nitrobenzaldehyde

Product 1

HCID 23444760(E)-3-[4-(benzyloxy)-3-nitrophenyl]-1-(2-hydroxy-5-methyl-3-nitrophenyl)-2-propen-1-oneYield 97%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2-hydroxy-5-methyl-3-nitroacetophenone (200 mg, 1.02 mmol), 4-benzyloxy-3-nitrobenzaldehyde (300 mg, 1.16 mmol) and 3 equivalents of sodium hydroxide (120 mg) were introduced into 80% aqueous ethanol solution and the resulting mixture was stirred for 3 hours at room temperature. The reaction solution was acidified by 2N hydrochloric acid solution and diluted with water. The resulting solid was filtered, washed with large amount of water and methanol, and then dried to give 430 mg (Yield 97%) of the title compound as a yellow solid.

Workup

  1. filtrationThe resulting solid was filtered
  2. washwashed with large amount of water and methanol
  3. customdried

Sources & evidence

ORD record
ord-bcc22993a6ac415384a846c59a8ed3d7
Source dataset
uspto-grants-2004_01
Patent number
US06683095B2

Reaction notes

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