Mesitylene → Anthracene

HRID 217548

Reaction equation

HRID 217548 reaction equation
C1(C)C=C(C)C=C(C)C=1.C([C:12]1[C:25]2[C:16](=[CH:17][C:18]3[C:23]([CH:24]=2)=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:15]=[CH:14][CH:13]=1)=C.C1(C=O)C2C(=CC3C(C=2)=CC=CC=3)C=CC=1>>[CH:15]1[C:16]2[C:25](=[CH:24][C:23]3[C:18]([CH:17]=2)=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 3

HCID 7947MesityleneHCID 35864Anthracenecarboxaldehyde2×HCID 139070581-Vinylanthracene2×

Product 1

HCID 8418Anthracene

Conditions

Temperature
150 °C

Procedure

Approximately 10 mmol mesitylene solution of vinylanthracene (VA) or anthraldehyde (AnA) was put in a round bottom flask and bubbled with nitrogen or argon gas for at least 30 min. A piece of the H-terminated silicon substrate was then immersed in the solution and allowed to react with VA or AnA for about 12 h under reflux at about 150° C. in an oil bath. During the reaction, the solution was also purged with nitrogen (or argon) to eliminate dissolved oxygen and to prevent the substrate from being oxidized. After the reaction, the substrate derivatized with VA or AnA was rinsed with dichloromethane, acetonitrile and methanol, and dried under a stream of nitrogen gas. The derivatization of the H-terminated surface with anthracene moieties as described in Example 3 is illustrated in FIG. 6.

Workup

  1. custombubbled with nitrogen or argon gas for at least 30 min
  2. customto react with VA or AnA for about 12 h
  3. customDuring the reaction
  4. customthe solution was also purged with nitrogen (or argon)
  5. dissolutionto eliminate dissolved oxygen
  6. customAfter the reaction
  7. washwas rinsed with dichloromethane, acetonitrile and methanol
  8. customdried under a stream of nitrogen gas

Sources & evidence

ORD record
ord-f58781bb35a2402ab83b7ad0e71ac9f1
Source dataset
uspto-grants-2012_06
Patent number
US08197650B2

Linked notes

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