Quinone → 2-(Diphenylphosphoryl)benzene-1,4-diol

HRID 968173Notes

Reaction equation

HRID 968173 reaction equation
[C:1]1(=[O:8])[CH:6]=[CH:5][C:4](=[O:7])[CH:3]=[CH:2]1.[C:9]1([PH:15](=[O:22])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1(C)C=CC=CC=1>[OH:7][C:4]1[CH:5]=[CH:6][C:1]([OH:8])=[CH:2][C:3]=1[P:15](=[O:22])([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 4650QuinoneHCID 254003Diphenylphosphine oxide

Product 1

HCID 27834952-(Diphenylphosphoryl)benzene-1,4-diol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Into a flame dried 2 L three neck round bottomed flask equipped with a mechanical stirrer, nitrogen gas inlet, pressure equalizing addition funnel, and drying tube were charged p-benzoquinone (30.16 g, 0.2790 mol) and toluene (750 mL). Diphenylphosphine oxide (56.42 g, 0.2790 mol) in toluene (250 mL) was added dropwise over 0.5 hour to the stirred solution at room temperature under nitrogen. The solution color changed from a dark brown to yellow with the formation of a gum. Upon further stirring, a grey solid formed. The solid was isolated, washed with toluene and then diethyl ether, and dried at 110° C. in flowing air to afford 74.0 g (85% crude yield) of an off-white solid. Recrystallization from ethanol afforded 2,5-dihydroxyphenyldiphenylphosphine oxide as a white solid (62.86 g, 73% recovery), m.p. 216-218° C.

Workup

  1. dry with materialInto a flame dried 2 L three neck round bottomed flask
  2. customequipped with a mechanical stirrer, nitrogen gas inlet
  3. additionaddition funnel
  4. customdrying tube
  5. customUpon further stirring, a grey solid formed
  6. customThe solid was isolated
  7. washwashed with toluene
  8. dry with materialdiethyl ether, and dried at 110° C.
  9. customto afford 74.0 g (85% crude yield) of an off-white solid
  10. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-298156e0153c474eb6d7216ddc4fd8b6
Source dataset
uspto-grants-2005_10
Patent number
US06958192B2

Reaction notes

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