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Quinone → 2,5-Dihydroxyphenyl(diphenyl)phosphine Oxide

HRID 968173
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HRID 968173 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 4650QuinoneHCID 254003Diphenylphosphine oxide

생성물 1

HCID 27834952,5-Dihydroxyphenyl(diphenyl)phosphine Oxide

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-298156e0153c474eb6d7216ddc4fd8b6
출처 데이터셋
uspto-grants-2005_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06958192B2

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