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

HRID 746337
Notes
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Reaction equation

HRID 746337 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

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.).

Workup

  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.

Sources & evidence

ORD record
ord-a9d5174c10ce4cf9a5b16df71b64ede7
Source dataset
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07393503B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes