Sodium Hydroxide → HCID 89751845, compound

HRID 1521810Notes

Reaction equation

HRID 1521810 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:19])[CH3:18])=[CH:13][C:12]=1[OH:20].[OH-].[Na+].[CH3:23][C:24]([CH3:49])([CH2:37]C1C=C(C)C=CC=1S([O-])(=O)=O)[CH2:25]C1C=C(C)C=CC=1S([O-])(=O)=O>CN(C=O)C>[CH3:23][C:24]1([CH3:49])[CH2:37][O:20][C:12]2[CH:13]=[C:14]([C:17](=[O:19])[CH3:18])[CH:15]=[CH:16][C:11]=2[C:3]2[CH:4]=[CH:5][C:6]([C:8](=[O:10])[CH3:9])=[CH:7][C:2]=2[O:1][CH2:25]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 58074814HCID 58074814, compoundHCID 131733111HCID 131733111, compound

Product 1

HCID 89751845HCID 89751845, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 1,1′-(2,2′-dihydroxy-[1,1′-biphenyl]-4,4′-diyl)-diethanone (0.2 g, 0.74 mmol) (synthesized according to WO 2010/111673) in anhydrous DMF (10 mL), NaOH (0.08 g, 1.85 mmol) and 2,2-dimethylpropane-1,3-diyl-bis-(4-methylbenzenesulfonate) (0.37 g, 0.89 mmol) (synthesized according to US 2005/0113374) were added successively and the suspension was stirred at 150° C. for 20 h under nitrogen atmosphere. The reaction mixture was brought to room temperature, crushed ice was added and stirred vigorously for 15 min. The contents were extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and purified by flash column chromatography (20% Ethyl acetate-Hexane) to yield a white solid (0.08 g, 32%). m/z 339.3 (M+H)+.

Workup

  1. customwas brought to room temperature
  2. customcrushed ice
  3. additionwas added
  4. stirringstirred vigorously for 15 min
  5. extractionThe contents were extracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over sodium sulfate
  8. custompurified by flash column chromatography (20% Ethyl acetate-Hexane)

Sources & evidence

ORD record
ord-aebbc88ab23b4bd28201a2f8e8f629bb
Source dataset
uspto-grants-2015_07
Patent number
US09073943B2

Reaction notes

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