Iodine → HCID 20519459, compound

HRID 2198534Notes

Reaction equation

HRID 2198534 reaction equation
[Mg].II.[Cl:4][C:5]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[C:6]=1[CH2:7]Cl.[Cl:14][CH2:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=1[Cl:25])=[O:17].[Cl-].[NH4+]>C(OCC)C>[CH:16]([O:17][CH:12]([CH3:11])[CH3:5])([CH3:18])[CH3:15].[Cl:4][C:5]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[C:6]=1[CH2:7][C:16]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=1[Cl:25])([OH:17])[CH2:15][Cl:14]

Participants

8

Reactant 5

HCID 807IodineHCID 202502,2',4'-TrichloroacetophenoneHCID 25517Ammonium ChlorideHCID 748322,6-Dichlorobenzyl chloride2×HCID 5462224Magnesium

Product 2

HCID 7914Diisopropyl EtherHCID 20519459HCID 20519459, compoundYield 654.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

5.35 g of magnesium chips and a little iodine are added to a solution of 3 g of 2,6-dichlorobenzyl chloride in 20 ml of diethyl ether. After brief heating, the reaction begins, after which another 36.1 g of 2,6-dichlorobenzyl chloride dissolved in 230 ml of diethyl ether are added dropwise at boiling temperature. A solution of 18.9 g of 2,2',4'-trichloroacetophenone in 150 ml of ether is then added dropwise, and the mixture left to react for 2 hours. The reaction mixture is then treated with an aqueous ammonium chloride solution, the ethereal phase is dried over sodium sulphate and concentrated in vacuo. Treatment of the solid residue with isopropyl ether gives 19.3 g of 1-(2,6-dichlorophenyl)-2-(2,4-dichlorophenyl)-3-chloropropan-2-ol melting at 117° C.

Workup

  1. additionare added dropwise
  2. waitthe mixture left
  3. customto react for 2 hours
  4. dry with materialthe ethereal phase is dried over sodium sulphate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a5439031bf1242cabfd6eb624acb0555
Source dataset
uspto-grants-1982_11
Patent number
US04358458

Reaction notes

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