Peracetic Acid → HCID 18759331, compound

HRID 434602Notes

Reaction equation

HRID 434602 reaction equation
[C:1](OO)(=[O:3])C.[I:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O.[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20]([OH:23])(=[O:22])=[O:21])=[CH:16][CH:15]=1.C1(OC)C=CC=CC=1>C(OCC)C.C(O)(=O)C>[S:20]([C:17]1[CH:18]=[CH:19][C:14]([CH3:24])=[CH:15][CH:16]=1)([O-:23])(=[O:22])=[O:21].[CH3:1][O:3][C:10]1[CH:11]=[CH:12][C:7]([IH+:6])=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 6585Peracetic AcidHCID 7519AnisoleHCID 11575IodobenzeneHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 18759331HCID 18759331, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

There was added dropwise, 45.6 grams (0.24 mole) of 40% peracetic acid to 20.4 grams (0.1 mole) of iodobenzene while the temperature was maintained at less than 30° C. After the addition of the peracid, there was added to the resulting mixture 19.05 grams (0.1 mole) of p-toluene sulfonic acid monohydrate, 10.8 grams (0.1 mole) of anisole and 10 ml of glacial acetic acid. The resulting mixture was stirred for 2 hours. The 4-methoxyphenyliodonium tosylate was isolated from the reaction mixture by trituration with diethyl ether, filtering and further washing with diethyl ether. There was obtained 41.8 grams or an 86.7% yield of a product having a melting point of 163°-165° C. Based on method of preparation, the product was 4-methoxyphenyliodonium tosylate.

Workup

  1. additionThere was added dropwise

Sources & evidence

ORD record
ord-84a2bce1a08b4e70991b1c71795b7af3
Source dataset
uspto-grants-1983_08
Patent number
US04399071

Reaction notes

Loading…