3-Methoxy-1,1':2',1''-terphenyl → 2-Methoxytriphenylene

HRID 467416Notes

Reaction equation

HRID 467416 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:10]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:6]=[CH:7][CH:8]=1>[Fe](Cl)(Cl)Cl.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:10]3[C:9](=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:5]=2[CH:4]=1

Participants

4

Reactant 1

HCID 161223163-Methoxy-1,1':2',1''-terphenyl

Product 1

HCID 587694502-MethoxytriphenyleneYield 60%

Reagents, catalysts & solvents 2

HCID 24380Iron chloride (FeCl3)CatalystHCID 6344DichloromethaneSolvent

Procedure

23.4 g of 3-methoxy[1,1′:2′,1″]terphenyl, 146 g of iron (III) chloride and 200 mL of methylene chloride were placed in a flask, and stirred for one hour while deaerating with argon. The reaction solution was subjected to filtration, followed by washing with an excessive amount of acetone. The resulting solid was dissolved in heated toluene. Insoluble substances were filtered out, followed by crystallization with cooling. The resulting crystal was collected by filtration to obtain 13.9 g (yield: 60%) of 2-methoxytriphenylene.

Workup

  1. filtrationThe reaction solution was subjected to filtration
  2. washby washing with an excessive amount of acetone
  3. dissolutionThe resulting solid was dissolved in heated toluene
  4. filtrationInsoluble substances were filtered out
  5. customfollowed by crystallization
  6. temperaturewith cooling
  7. filtrationThe resulting crystal was collected by filtration

Sources & evidence

ORD record
ord-b2224c9c4deb4cde88f2e91f24b2fb9e
Source dataset
uspto-grants-2014_01
Patent number
US08623520B2

Reaction notes

Loading…