Octyl phenyl ether → Octyl phenyl ether

HRID 613588Notes

Reaction equation

HRID 613588 reaction equation
O[C:2]1[C:3]([O:9][S:10]([C:13]2[CH:19]=[CH:18][C:16](C)=[CH:15][CH:14]=2)(=[O:12])=[O:11])=[C:4]([I:8])[CH:5]=[CH:6][CH:7]=1.[CH2:20]([O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>C(#N)C.C(O)(=O)C>[C:19]1([CH3:20])[C:13]([S:10]([O-:9])(=[O:11])=[O:12])=[CH:14][CH:15]=[CH:16][CH:18]=1.[CH2:20]([O:28][C:29]1[CH:30]=[CH:31][C:32]([I+:8][C:4]2[CH:3]=[CH:2][CH:7]=[CH:6][CH:5]=2)=[CH:33][CH:34]=1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].[CH2:20]([O:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

6

Reactant 2

HCID 74558Octyl phenyl etherHCID 21918218Hydroxy tosyloxy iodobenzene

Product 2

HCID 74558Octyl phenyl etherHCID 86754986HCID 86754986, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolvent

Procedure

A sample of (4-octyloxyphenyl)phenyl iodonium toluenesulfonate (in short C8-O-iodonium) was prepared according to the method of Crivello et al (J. Polym. Sci: Part A: Polymer Chemistry, (1989), 27, 3951-3968) by reacting hydroxytosyloxyiodobenzene with octyloxybenzene in a mixture of acetonitrile and acetic acid. Octyloxybenzene was previously obtained by reacting sodium phenate with bromooctane in a water/toluene mixture by phase transfer catalysis in the presence of tetrabutyl ammonium bromide. To 8 g of this compound in solution in 60 ml of methylethylketone (MEK) are added 3.02 of potassium bis-fluorosulfonylimide. The mixture is stirred magnetically for 1 hour at room temperature and filtrated to remove the insoluble potassium toluenesulfonate. The solution is poured into a flask which is adjusted to be adapted on a rotary evaporator and the solvent is evaporated. The last traces of MEK are eliminated under a vacuum primary pump and the residue is in the form of a viscous oil (8.04 g, 98%). There is added thereto an equal weight of dichloromethane enabling to give a fluid mixture which can be handled. Solubility tests are made in adjusted flasks after adding a given quantity of mixture and evaporation of the volatile fraction (CH2Cl2). Results of the tests are given below:

Sources & evidence

ORD record
ord-2a4383c763444a2ab5cbedf0f396f57e
Source dataset
uspto-grants-1999_12
Patent number
US06008265

Reaction notes

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