Methyl iodide → HCID 11148076, compound

HRID 1828252Notes

Reaction equation

HRID 1828252 reaction equation
[CH:1]([O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=1)([CH3:3])[CH3:2].[Mg].I[CH3:15].[Cl-].[NH4+]>C(OCC)C.O>[CH:1]([O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]([OH:10])[CH3:15])=[CH:7][CH:6]=1)([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 2500774-IsopropoxybenzaldehydeHCID 5462224Magnesium

Product 1

HCID 11148076HCID 11148076, compoundYield 92.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 4-isopropyloxy benzaldehyde of formula 5 (5 g, 30 mmol) in dry diethyl ether is slowly added to an ethereal solution of Grignard reagent prepared from magnesium metal (0.84 g, 35 mmol) and iodomethane (2.6 ml, 40 mmol) and the contents stirred for 1 hour at room temperature. After the completion of the reaction, the mixture is worked up by adding saturated aqueous solution of ammonium chloride (10 ml), followed by dilution with water (100 ml), separating the organic layer and extracting the aqueous layer with solvent ether (2×100 ml). The combined organic layer is washed with water (2×20 ml), dried over anhydrous sodium sulphate and concentrated in vacuo to yield 1-(4-isopropyloxy phenyl) ethanol, in a semisolid of general formula 4 in 92.5% yield.

Workup

  1. customAfter the completion of the reaction
  2. customseparating the organic layer
  3. extractionextracting the aqueous layer with solvent ether (2×100 ml)
  4. washThe combined organic layer is washed with water (2×20 ml)
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cd846c3a367245718adf505a84e636b1
Source dataset
uspto-grants-2006_06
Patent number
US07057040B2

Reaction notes

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