Hexane → HCID 12950401, compound

HRID 2108258Notes

Reaction equation

HRID 2108258 reaction equation
C([Li])CCC.CCCCCC.[CH3:12][O:13][C:14]1[C:19]([O:20][CH3:21])=[CH:18][CH:17]=[CH:16][C:15]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[Br:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]Br>O1CCCC1>[CH3:12][O:13][C:14]1[C:19]([O:20][CH3:21])=[CH:18][CH:17]=[CH:16][C:15]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[Br:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:18]1[CH:17]=[CH:16][C:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:14]([O:13][CH3:12])[C:19]=1[O:20][CH3:21]

Participants

7

Reactant 4

HCID 8058HexaneHCID 123681,6-DibromohexaneHCID 12950401HCID 12950401, compoundHCID 178418339Butyllithium

Product 2

HCID 12950401HCID 12950401, compoundHCID 14986384HCID 14986384, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2.5M butyl lithium in hexane (16 mL, 0.04 mol) was added dropwise over 15 min. to a stirred solution of 8.3 g (0.039 mol) of 2,3-dimethoxybiphenyl [J. M. Bruce and F. K. Sutcliffe, J. Chem. Soc. 4435 (1955)] in 160 mL of anhydrous tetrahydrofuran cooled at 0° under argon. The reaction mixture was stirred at 0° for 2.5 hours and then refluxed for 30 min. After cooling to 5°, 6.3 mL (0.039 mole) of 1,6-dibromohexane was added. Stirring was continued at 5° for 30 min. at 25° for 30 min. and at reflux for 20 hours. Workup as in Example 1 gave an oil. Purification by HPLC using 3% ethyl acetatehexane gave 5.7 g of unreacted 2,3-dimethoxybiphenyl and 3.3 g of 4-(6-bromohexyl)-2,3-dimethoxy-1,1'-biphenyl as an oil. The structure was confirmed by the nmr and mass spectra (molecular ion at m/e 376).

Workup

  1. temperaturecooled at 0° under argon
  2. temperaturerefluxed for 30 min
  3. temperatureAfter cooling to 5°
  4. stirringStirring
  5. waitwas continued at 5° for 30 min. at 25° for 30 min.
  6. temperatureat reflux for 20 hours
  7. customWorkup as in Example 1 gave an oil
  8. customPurification by HPLC

Sources & evidence

ORD record
ord-897553420442467d9a4d8a3b46ff550f
Source dataset
uspto-grants-1990_06
Patent number
US04937373

Reaction notes

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