1,4-Dimethoxybenzene → 1,4-Dimethoxy-6,7,10,11-tetrakis(decyloxy)triphenylene

HRID 217582

반응식

HRID 217582 반응식
[CH2:1]([O:11][C:12]1[CH:13]=[C:14]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])=[C:31]([O:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56])[CH:30]=2)[CH:15]=[CH:16][C:17]=1[O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[CH3:57][O:58][C:59]1[CH:64]=[CH:63][C:62]([O:65][CH3:66])=[CH:61][CH:60]=1>C(Cl)Cl>[CH3:57][O:58][C:59]1[C:64]2[C:34]3[C:29](=[CH:30][C:31]([O:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56])=[C:32]([O:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[CH:33]=3)[C:14]3[C:15](=[CH:16][C:17]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[C:12]([O:11][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH:13]=3)[C:63]=2[C:62]([O:65][CH3:66])=[CH:61][CH:60]=1

참가 물질

4

반응물 2

HCID 90161,4-DimethoxybenzeneHCID 154737493,3',4,4'-Tetrakis(decyloxy)-1,1'-biphenyl

생성물 1

HCID 536909211,4-Dimethoxy-6,7,10,11-tetrakis(decyloxy)triphenylene수율 84%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Solid 3a (5.50 g, 7.06 mmol) was added to an ice cold suspension of anhydrous FeCl3 (9.16 g, 56.5 mmol) in dry CH2Cl2 (250 mL). Within 2 min 1,4-dimethoxybenzene (3.90 g, 28.2 mmol) was added to the green reaction mixture. The reaction mixture was allowed to warm slowly to room temperature and then stir for an additional 12 h. The reaction mixture was quenched with anhydrous MeOH (30 mL). The volume of the mixture was reduced to 50 mL under reduced pressure and MeOH (200 mL) was added to the resulting oil. The slightly violet product was colled on a frit and washed with MeOH. The product was further purified by column chromatography using a 50% CH2Cl2/50% hexane solvent mixture to afford 4a (RF=0.24) as a colorless solid in 84% yield (mp 69-70° C.).

후처리

  1. customThe reaction mixture was quenched with anhydrous MeOH (30 mL)
  2. additionwas added to the resulting oil
  3. washwashed with MeOH
  4. customThe product was further purified by column chromatography

출처 및 근거

ORD 기록
ord-e5627bed7fb743cc8452b252aec2f8dd
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198096B2

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