4,4'-Dihydroxybiphenyl → 4,4'-Diacetoxybiphenyl

HRID 1460718Notes

Reaction equation

HRID 1460718 reaction equation
[C:1]1([OH:14])[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)=[CH:3][CH:2]=1>C(OC(=O)C)(=O)C>[C:10]([O:14][C:1]1[CH:2]=[CH:3][C:4]([C:7]2[CH:12]=[CH:11][C:10]([O:13][C:1](=[O:14])[CH3:2])=[CH:9][CH:8]=2)=[CH:5][CH:6]=1)(=[O:13])[CH3:9]

Participants

3

Reactant 1

HCID 71124,4'-Dihydroxybiphenyl

Product 1

HCID 6042814,4'-DiacetoxybiphenylYield 185.6%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
-15 °C

Procedure

An amount of 4,4'-biphenol (200 g, 1.07 moles), (Aldrich Chemical Company, Milwaukee, Wis.), and 1000 ml of acetic anhydride were added to a 2-liter boiling flask equipped with a cold water condenser and a polytetrafluoroethylene-coated magnetic stirring bar. The mixture was heated to reflux under nitrogen and all of the solid dissolved. The solution was refluxed for 20 hours, then cooled in a freezer at -15° C. overnight. The white crystals that were formed were isolated by filtration, washed with cold acetic anhydride and dried in a 100° C. vacuum oven overnight yielding 268.4 g of 4,4'-diacetoxybiphenyl with a m.p. of 162.7° C. to 164.0° C.

Workup

  1. customequipped with a cold water condenser and a polytetrafluoroethylene-coated magnetic stirring bar
  2. temperatureThe mixture was heated
  3. temperatureto reflux under nitrogen
  4. dissolutionall of the solid dissolved
  5. temperatureThe solution was refluxed for 20 hours
  6. customThe white crystals that were formed
  7. customwere isolated by filtration
  8. washwashed with cold acetic anhydride
  9. customdried in a 100° C. vacuum oven overnight

Sources & evidence

ORD record
ord-2d58630a1af2483fb5a5c2e99ee363f0
Source dataset
uspto-grants-1991_12
Patent number
US05071942

Reaction notes

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