Monobenzone → HCID 22120960, compound

HRID 607248Notes

Reaction equation

HRID 607248 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[CH2:13]([O:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>N1C=CC=CC=1>[CH2:13]([O:20][C:21]1[CH:22]=[CH:23][C:24]([O:27][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=2[N+:10]([O-:12])=[O:11])=[CH:25][CH:26]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 7638MonobenzoneHCID 11430Potassium CarbonateHCID 855054-Chloro-3-nitrobenzaldehyde

Product 1

HCID 22120960HCID 22120960, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 4-chloro-3-nitrobenzaldehyde (1.00 g, 5.389 mmol), 4-(benzyloxy)phenol (1.187 g, 5.928 mmol), and potassium carbonate (0.744 g, 5.389 mmol) in anhydrous pyridine (10 mL) was heated at reflux under a nitrogen atmosphere for 30 minutes. The reaction was cooled to room temperature and the solvent removed by rotary evaporation under vacuum. The residue was taken up in ethyl acetate (100 mL) and washed with 1N aqueous hydrochloric acid (2×50 mL), water (50 mL), and brine (50 mL). The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. Purification by silica gel flash chromatography using methylene chloride as eluent provided the title compound as a yellow solid (1.625 g, 86%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux under a nitrogen atmosphere for 30 minutes
  3. customthe solvent removed by rotary evaporation under vacuum
  4. washwashed with 1N aqueous hydrochloric acid (2×50 mL), water (50 mL), and brine (50 mL)
  5. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customPurification by silica gel flash chromatography

Sources & evidence

ORD record
ord-480058fdb11848c59c8dc669527c2be3
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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