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Tetrahydrofuran → 3,3',4,4'-Tetrakis(decyloxy)-1,1'-biphenyl

HRID 1257948
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Reaktionsgleichung

Reaktionsgleichung von HRID 1257948
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[Li][CH2:8][CH2:9][CH2:10][CH3:11].[CH2:12]1[CH2:16][O:15][CH2:14][CH2:13]1.Br[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[C:20]([O:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[CH:19]=1>O>[CH2:1]([O:24][C:21]1[CH:20]=[C:19]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[C:20]([O:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[CH:19]=2)[CH:18]=[CH:12][C:16]=1[O:15][CH2:14][CH2:13][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH3:25])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:8][CH2:9][CH2:10][CH3:11]
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Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 8058HexaneHCID 178485934-Bromo-1,2-bis(decyloxy)benzeneHCID 178418339Butyllithium

Produkt 1

HCID 154737493,3',4,4'-Tetrakis(decyloxy)-1,1'-biphenylAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel

Versuchsvorschrift

A hexane solution of nBuLi (1.57 M, 1.02 mL) was added dropwise to a THF solution (50 mL) of 2a which had been precooled to −30° C. Once the addition was complete the reaction mixture was allowed to warm to room temperature. After stirring for an additional 12 h the reaction mixture was poured into water and extracted with ether. The ether layer was washed with water and dried with MgSO4. The solvent was removed under reduced pressure. The residue was crystallized from a THF/MeOH mixture at −15° C. to give colorless crystals of 3,3′,4,4′-tetrakisdecyloxybiphenyl (3a) in 38% yield (mp 85-86° C.).

Aufarbeitung

  1. customhad been precooled to −30° C
  2. additionOnce the addition
  3. extractionextracted with ether
  4. washThe ether layer was washed with water
  5. dry with materialdried with MgSO4
  6. customThe solvent was removed under reduced pressure
  7. customThe residue was crystallized from a THF/MeOH mixture at −15° C.

Quellen und Nachweise

ORD-Eintrag
ord-ff35ada6f55947e4b75f107db4525829
Quelldatensatz
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08465678B2

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