4,4'-Dihydroxybenzophenone → HCID 10200771, compound

HRID 1190769Notes

Reaction equation

HRID 1190769 reaction equation
[OH:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=O)=[CH:4][CH:3]=1>C1COCC1.Cl[Ti](Cl)(Cl)Cl.[Zn]>[OH:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[C:6]([C:5]2[CH:15]=[CH:16][C:2]([OH:1])=[CH:3][CH:4]=2)[C:8]2[CH:9]=[CH:10][C:11]([OH:14])=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 691504,4'-Dihydroxybenzophenone

Product 1

HCID 10200771HCID 10200771, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 24193Titanium TetrachlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 4,4′-dihydroxybenzophenone (3.0 g, 14.0 mmol), 1 equiv of TiCl4 (1.54 ml, 14.0 mmol), and 2 equiv of Zn dust (1.83 g, 28.0 mmol) in 100 ml of dry THF was refluxed for 20 h. The reaction mixture was cooled to room temperature and filtered. The filtrates were evaporated and the crude product was purified by a silica gel column using ethyl acetate (EA) as eluent. DHTPE was obtained as slight yellow powder of 83% yield.

Workup

  1. temperaturewas refluxed for 20 h
  2. filtrationfiltered
  3. customThe filtrates were evaporated
  4. customthe crude product was purified by a silica gel column
  5. customDHTPE was obtained as slight yellow powder of 83% yield

Sources & evidence

ORD record
ord-dc95d5329b9e435bbdd561a89ded2aa0
Source dataset
uspto-grants-2014_03
Patent number
US08679738B2

Reaction notes

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