Sodium Acetate → HCID 225284, compound

HRID 1449291Notes

Reaction equation

HRID 1449291 reaction equation
C([C:5]1[CH:6]=[C:7]([CH:16]([C:19]2[CH:24]=[C:23]([C:25]([CH3:28])([CH3:27])[CH3:26])[C:22]([OH:29])=[C:21]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH:20]=2)CCl)C=C(C(C)(C)C)C=1O)(C)(C)C.[C:34]([O-:37])(=O)[CH3:35].[Na+]>C(O)(=O)C>[C:30]([C:21]1[CH:20]=[C:19]([CH:16]=[CH:7][C:6]2[CH:5]=[C:35]([C:23]([CH3:25])([CH3:24])[CH3:22])[C:34]([OH:37])=[C:21]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH:20]=2)[CH:24]=[C:23]([C:25]([CH3:27])([CH3:26])[CH3:28])[C:22]=1[OH:29])([CH3:32])([CH3:31])[CH3:33]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 20350728HCID 20350728, compound

Product 1

HCID 225284HCID 225284, compoundYield 162.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a 100 milliliter round-bottomed flask equipped with a magnetic stirrer and a reflux condenser capped with a paraffin-sealed gas bubbler was added 9.45 grams (0.022 mole) of 1,1-bis(3,5-di-t-butyl-4-hydroxyphenyl)-2-chloroethane (from EXAMPLE 10 above), 20 milliliters of glacial acetic acid, and 2.0 grams (0.024 mole) of anhydrous sodium acetate. The mixture was stirred and heated to reflux for 4 hours. The resulting homogeneous solution was cooled to ambient temperatures to induce crystallization of the product. The precipitated solid material was collected by suction filtration, washed successively with acetic acid and water, and dried to yield 7.8 grams (90 percent) of 3,5,3',5'-tetra-t-butyl-4,4'-dihydroxystilbene, which identity was confirmed by nuclear magnetic resonance spectroscopy.

Workup

  1. customTo a 100 milliliter round-bottomed flask equipped with a magnetic stirrer and a reflux condenser
  2. customsealed gas bubbler
  3. temperatureheated
  4. temperatureto reflux for 4 hours
  5. temperatureThe resulting homogeneous solution was cooled to ambient temperatures
  6. customcrystallization of the product
  7. filtrationThe precipitated solid material was collected by suction filtration
  8. washwashed successively with acetic acid and water
  9. customdried

Sources & evidence

ORD record
ord-bdc9a422ffc74725a044074a52a19942
Source dataset
uspto-grants-1980_02
Patent number
US04189610

Reaction notes

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