Potassium → Bis(4-t-butylphenyl)iodonium 9,10-diethoxyanthracene-2-sulfonate

HRID 1421204Notes

Reaction equation

HRID 1421204 reaction equation
C([O-])(=O)C.[C:5]([C:9]1[CH:14]=[CH:13][C:12]([I+:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:18][CH:17]=2)=[CH:11][CH:10]=1)([CH3:8])([CH3:7])[CH3:6].[CH2:26]([O:28][C:29]1[C:30]2[C:35]([C:36]([O:47][CH2:48][CH3:49])=[C:37]3[C:42]=1[CH:41]=[C:40]([S:43]([OH:46])(=[O:45])=[O:44])[CH:39]=[CH:38]3)=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH3:27].[K]>>[CH2:26]([O:28][C:29]1[C:30]2[C:35]([C:36]([O:47][CH2:48][CH3:49])=[C:37]3[C:42]=1[CH:41]=[C:40]([S:43]([O-:46])(=[O:44])=[O:45])[CH:39]=[CH:38]3)=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH3:27].[C:22]([C:19]1[CH:20]=[CH:21][C:16]([I+:15][C:12]2[CH:11]=[CH:10][C:9]([C:5]([CH3:8])([CH3:7])[CH3:6])=[CH:14][CH:13]=2)=[CH:17][CH:18]=1)([CH3:25])([CH3:24])[CH3:23]

Participants

4

Reactant 3

HCID 5462222PotassiumHCID 187804029,10-Diethoxyanthracene-2-sulfonic acidHCID 21909498Iodonium, bis[4-(1,1-dimethylethyl)phenyl]-, acetate

Product 1

HCID 18780401Bis(4-t-butylphenyl)iodonium 9,10-diethoxyanthracene-2-sulfonate

Procedure

Preparation of bis(4-t-butylphenyl)iodonium 9,10-diethoxyanthracene-2-sulfonate according to Formula 2 above wherein R3 and R4 are both t-butyl and OR5 and OR6 are both ethoxy is as follows. A slurry of 399 g potassium periodate (1.86 M) was prepared in a pre-made solution of 761 g (705 mL, 7.45 M) acetic anhydride in 500 g (577 mL, 3.725 M) of t-butylbenzene using mechanical stirring. While cooling with ice bath, 402 g (4.1 M) of concentrated H2SO4 was added slowly, maintaining the temperature at 25±5° C. (approximately 2 hours). The reaction was allowed to stir overnight, allowing ice to melt in bath. The next day the reaction was re-cooled to 0-10° C. and a total of 1.25 L H2O added. Initially the reaction was very exothermic, but as the addition proceeded the water was added more rapidly. 252 mL of ammonium hydroxide was added next, followed by 1.5 L dichloromethane. The water layer was discarded, and the dichloromethane layer washed several times with water. The dichloromethane layer was dried with magnesium sulfate and filtered, then evaporated to a low volume on a rotary evaporate to induce crystallization. The solid was filtered and rinsed with toluene and sucked dry. The residue was recrystallized from IPA to yield 243 g of a white solid of bis(4-t-butylphenyl)iodonium acetate. The bis(4-t-butylphenyl)iodonium acetate may then be combined under suitable conditions known in the art with 9,10-diethoxyanthracene-2-sulfonic acid, potassium salt to yield bis(4-t-butylphenyl)iodonium 9,10-diethoxyanthracene-2-sulfonate. Alternatively, 9,10-dimethoxyanthracene-2-sulfonic acid, potassium salt may be used to yield a sulfonium salt according to Formula 2 wherein OR5 and OR6 are both methoxy.

Sources & evidence

ORD record
ord-0d0289bb8c47428f8d0ed7eeaf2e583c
Source dataset
uspto-grants-2000_06
Patent number
US06074800

Reaction notes

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