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Sodium Hydroxide → 4-Hydroxy-3-(3-methoxy-phenyl)-butyric acid benzhydrylidene-hydrazide

HRID 8201
Notes
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Reaction equation

HRID 8201 reaction equation
C[Al](C)C.[C:5](=[N:18][NH2:19])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH:28]2[CH2:32][O:31][C:30](=[O:33])[CH2:29]2)[CH:25]=[CH:26][CH:27]=1.[OH-].[Na+]>ClCCl>[C:5](=[N:18][NH:19][C:30](=[O:33])[CH2:29][CH:28]([C:24]1[CH:25]=[CH:26][CH:27]=[C:22]([O:21][CH3:20])[CH:23]=1)[CH2:32][OH:31])([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 79304DiphenylmethylidenehydrazineHCID 16682925TrimethylaluminumHCID 693646374-(3-Methoxyphenyl)oxolan-2-one

Product 1

HCID 865926214-Hydroxy-3-(3-methoxy-phenyl)-butyric acid benzhydrylidene-hydrazide

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
3×

Procedure

Trimethylaluminum (12 mL, 2 M in hexane, 24 mmol) is added dropwise to a solution of benzophenone hydrazone (1.57 g, 8 mmol) in dichloromethane (20 mL) at room temperature and under nitrogen. After the mixture is stirred for 30 min, 4-(3-methoxy-phenyl)-dihydro-furan-2-one, (1.54 g, 8 mmol) in dichloromethane (5 mL) is added. The mixture is refluxed for 5 h cooled to room temperature and diluted with dichloromethane (30 mL). The mixture is treated with 4 N sodium hydroxide (30 mL) and stirred one hour. The organic layer is separated, washed with brine and, dried over magnesium sulfate. The mixture is filtered, concentrated in vacuo and chromatographed on SiO2 (2% methanol/dichloromethane) to yield the title compound, 2.25 g (73%) as a pale yellow oil.

Workup

  1. temperatureThe mixture is refluxed for 5 h
  2. stirringstirred one hour
  3. customThe organic layer is separated
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationThe mixture is filtered
  7. concentrationconcentrated in vacuo
  8. customchromatographed on SiO2 (2% methanol/dichloromethane)

Sources & evidence

ORD record
ord-9cd95b0817f941b7980e1a771dfd5afc
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07087626B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes