2,2',4,4'-Tetrahydroxybenzophenone → 680610-92-8

HRID 1294891Notes

Reaction equation

HRID 1294891 reaction equation
O[C:2]1[CH:17]=[C:16]([OH:18])[CH:15]=[CH:14][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:7]=1[OH:13])=O.C([O-])(=O)C.[Na+].C(O)(=O)C(O)=O.[CH2:30]([NH:32][NH2:33])[CH3:31]>O>[CH2:30]([N:32]1[C:2]2[C:3](=[CH:14][CH:15]=[C:16]([OH:18])[CH:17]=2)[C:4]([C:6]2[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:7]=2[OH:13])=[N:33]1)[CH3:31]

Participants

5

Reactant 3

HCID 85712,2',4,4'-TetrahydroxybenzophenoneHCID 96181Hydrazine, ethyl-, ethanedioate (1:1)HCID 517045Sodium Acetate

Product 1

HCID 135438183680610-92-8Yield 18.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2,2′,4,4′-tetrahydroxybenzophenone (0.123 g, 0.5 mmol), sodium acetate (0.164 g, 2.0 mmol) and ethylhydrazine oxalate (0.30 g, 2.0 mmol) in 2 mL H2O was heated at 90° C. overnight. The cooled reaction mixture was partitioned with EtOAc and 1 N HCl. The organic layer was dried (Na2SO4) and concentrated in vacuo to give the crude product. The residue was purified by HPLC chromatography using a silica gel column 150×12 mm (Biotage) at 10 mL/min with methyl-t-butyl ether/hexane (1:3, v/v) to give 0.025 g of product as an off-white solid.

Workup

  1. customThe cooled reaction mixture
  2. customwas partitioned with EtOAc and 1 N HCl
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customto give the crude product
  6. customThe residue was purified by HPLC chromatography

Sources & evidence

ORD record
ord-dc67e9203fff41a18b54546c4f0e6355
Source dataset
uspto-grants-2007_07
Patent number
US07241791B2

Reaction notes

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