1,4-Dioxane → HCID 19593360, compound

HRID 613590Notes

Reaction equation

HRID 613590 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH:2]=[CH2:3].C1([C:17]2[C:18]([I:28]=O)=[C:19]([S:24]([O-:27])(=[O:26])=[O:25])[C:20]([CH3:23])=[CH:21][CH:22]=2)C=CC=CC=1.O1CCOCC1>C(O)(=O)C>[C:20]1([CH3:23])[C:19]([S:24]([O-:27])(=[O:26])=[O:25])=[CH:18][CH:17]=[CH:22][CH:21]=1.[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[I+:28][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:17]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 74458Allyl phenyl etherHCID 86754987HCID 86754987, compound

Product 1

HCID 19593360HCID 19593360, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To 40 g of allyloxybenzene in 50 ml of acetic acid are added dropwise 78.4 g of phenyliodosotoluene sulfonate in 100 ml of acetic acid and the mixture is stirred at room temperature for 2 hours. The reaction mixture is poured into 1l of dioxane, the precipitate of (allyloxyphenyl)-phenyliodonium toluenesulfonate obtained is washed with ether and dried. Conversion into bis-fluorosulfonylimide is carried out by mixing 15 g of (allyloxyphenyl)-phenyliodonium toluenesulfonate and 7 g of KN(SO2F)2 in 150 ml of water at 0° C. The salt is extracted with 2×50 ml of dichloromethane and the solvent is evaporated. The residual salt (consisting of (allyloxyphenyl)-phenyliodonium bis-fluorosulfonylimide) is diluted with 60 ml of THF and is introduced into a three-neck flask provided with a cooler, a mechanical stirrer and a neutral gas inlet (Argon), said flask containing 8.5 g of a copolymer of dimethylsiloxane and (hydrogeno)(methyl)-siloxane (HMS 301 25% SiH, Mw 1900 sold by Gelest Inc., Tullytown, Pa., U.S.A.) in solution in 60 ml of THF and 90 mg of chloroplatinic acid H2PtCl6. The mixture was heated under reflux for 2 hours. 1 g of 1-hexene was thereafter added and the reaction was continued for 1 hour. A sampling enables to confirm the complete disappearance of IR bands of the SiH bond which confirms hydrosilylation between the allyl groups of (allyloxyphenyl)-phenyliodonium bis-fluorosulfonylimide and groups SiH of the copolymer of dimethylsiloxane and (hydrogeno)(methyl)-siloxane. The polymer thus obtained which contains ionic pendant groups is precipitated in methanol and purified by means of three operations of dissolution (THF)/precipitation (methanol and ether).

Sources & evidence

ORD record
ord-5f5a01cdb7534933b995fcd6b9887d11
Source dataset
uspto-grants-1999_12
Patent number
US06008265

Reaction notes

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