Dimethylformamide → 2,3,6,7,10,11-Hexa(4-methylhexyloxy)triphenylene

HRID 1274792Notes

Reaction equation

HRID 1274792 reaction equation
CN(C)C=O.[H-].[Na+].[OH:8][C:9]1[C:26]([OH:27])=[CH:25][C:24]2[C:23]3[C:18](=[CH:19][C:20]([OH:29])=[C:21]([OH:28])[CH:22]=3)[C:17]3[C:12](=[CH:13][C:14]([OH:31])=[C:15]([OH:30])[CH:16]=3)[C:11]=2[CH:10]=1.C1(C)C=CC(S(O[CH2:42][CH2:43][CH2:44][CH:45]([CH3:48])[CH2:46][CH3:47])(=O)=O)=CC=1>O>[CH3:48][CH:45]([CH2:46][CH3:47])[CH2:44][CH2:43][CH2:42][O:8][C:9]1[C:26]([O:27][CH2:42][CH2:43][CH2:44][CH:45]([CH3:48])[CH2:46][CH3:47])=[CH:25][C:24]2[C:23]3[C:18](=[CH:19][C:20]([O:29][CH2:15][CH2:16][CH2:17][CH:18]([CH3:23])[CH2:19][CH3:20])=[C:21]([O:28][CH2:42][CH2:43][CH2:44][CH:45]([CH3:48])[CH2:46][CH3:47])[CH:22]=3)[C:17]3[C:12](=[CH:13][C:14]([O:31][CH2:42][CH2:43][CH2:44][CH:45]([CH3:48])[CH2:46][CH3:47])=[C:15]([O:30][CH2:26][CH2:9][CH2:10][CH:11]([CH3:12])[CH2:24][CH3:25])[CH:16]=3)[C:11]=2[CH:10]=1

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 110886102,3,6,7,10,11-HexahydroxytriphenyleneHCID 134634484-Methylhexyl p-toluenesulfonate

Product 1

HCID 221181212,3,6,7,10,11-Hexa(4-methylhexyloxy)triphenyleneYield 56.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

At room temperature, 3 ml of N,N-dimethylformamide (DMF) was placed in a flask, and 0.27 g of NaH (60% in oil) was added thereto. Then, 0.3 g (0.925 mmol) of 2,3,6,7,10,11-hexahydroxytriphenylene was added thereto, and after 1 hour of stirring, a mixture liquid of 1.96 g (6.84 mmol) of 4-methylhexyl p-toluenesulfonate and 2 ml of DMF was added dropwise thereto, followed by 5 hours of stirring at 70° C. After the reaction, the system was cooled to room temperature, and water was added thereto to precipitate a crystal, which was recovered by filtration. The crystal was then purified by silica gel chromatography (with toluene) and re-cystallized from acetone/methanol to obtain 0.24 g of 2,3,6,7,10,11-hexa(4-methylhexyloxy)triphenylene.

Workup

  1. waitfollowed by 5 hours
  2. stirringof stirring at 70° C
  3. customAfter the reaction
  4. customto precipitate a crystal, which
  5. filtrationwas recovered by filtration
  6. customThe crystal was then purified by silica gel chromatography (with toluene) and re-cystallized from acetone/methanol

Sources & evidence

ORD record
ord-22365e5b33404a10bc7594ca22279511
Source dataset
uspto-grants-2000_12
Patent number
US06159562

Reaction notes

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