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

HRID 1271802Notes

Reaction equation

HRID 1271802 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]

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 962WaterSolvent

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-65bdffb4b0e94485a2fd5dac9ea57cc8
Source dataset
uspto-grants-2007_04
Patent number
US07208122B2

Reaction notes

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