Sodium Iodide → 1-(4-Hydroxy-3,5-di-isopropylphenyl)-2-iodo-ethanone

HRID 1163457Notes

Reaction equation

HRID 1163457 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:10]=[C:9]([CH:11]([CH3:13])[CH3:12])[C:8]([OH:14])=[C:7]([CH:15]([CH3:17])[CH3:16])[CH:6]=1)=[O:4].[I-:18].[Na+].CCCCCC>COCCOC>[OH:14][C:8]1[C:9]([CH:11]([CH3:13])[CH3:12])=[CH:10][C:5]([C:3](=[O:4])[CH2:2][I:18])=[CH:6][C:7]=1[CH:15]([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 8058HexaneHCID 858900592-Chloro-1-(4-hydroxy-3,5-di-isopropylphenyl)-ethanone

Product 1

HCID 577472361-(4-Hydroxy-3,5-di-isopropylphenyl)-2-iodo-ethanoneYield 70%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a solution of 50.95 g (200 mmol) of 2-chloro-1-(4-hydroxy-3,5-di-isopropylphenyl)-ethanone in 250 ml of 1,2-dimethoxyethane, a solution of 30.94 g (206 mmol) of sodium iodide in 250 ml of 1,2-dimethoxyethane is added dropwise at room temperature. After the addition, stirring is continued for 16 hours at room temperature. Then 100 ml of hexane is added and, after stirring for additional 15 minutes, the precipitated salts are removed by filtration. The obtained solution is evaporated and the resulting residue is purified by recrystallization from hexane/dichloromethane to give 48.5 g (70%) of compound 201, m.p. 127-128° C.

Workup

  1. additionAfter the addition
  2. stirringafter stirring for additional 15 minutes
  3. customthe precipitated salts are removed by filtration
  4. customThe obtained solution is evaporated
  5. customthe resulting residue is purified by recrystallization from hexane/dichloromethane

Sources & evidence

ORD record
ord-dfe52df670cf4c17b912d63c42a70261
Source dataset
uspto-grants-2010_10
Patent number
US07820865B2

Reaction notes

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