Methyl iodide → 1-Iodo-3-methyloct-1-en-3-ol

HRID 427072Notes

Reaction equation

HRID 427072 reaction equation
[Mg].[CH3:2]I.[I:4][CH:5]=[CH:6][C:7](=[O:13])[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[Cl-].[NH4+]>CCOCC>[OH:13][C:7]([CH3:2])([CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH:6]=[CH:5][I:4]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 534008741-Iodooct-1-en-3-one

Product 1

HCID 545226831-Iodo-3-methyloct-1-en-3-olYield 86.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

To a Grignard solution preapred from 1.05 g (0.41 moles) of magnesium and 6.2 g (0.435 moles) of methyl iodide in 30 ml of dry ether under argon is added dropwise 10 g of 1-iodo-1-octen-3-one (Example 183) in 45 ml of ether. The resulting solution is stirred at ambient temperature for one hour. After the addition of 75 ml of saturated ammonium chloride the ether layer is separated and the aqueous layer is separated and the aqueous layer is extracted several times with ether. The combined ether extracts are washed successively with ammonium chloride and water, dried and taken to dryness to give 9.24 g of product as an oil; λ max 2.89, 3.23, 6.24 and 10.5.

Workup

  1. customis separated
  2. customthe aqueous layer is separated
  3. extractionthe aqueous layer is extracted several times with ether
  4. washThe combined ether extracts are washed successively with ammonium chloride and water
  5. customdried

Sources & evidence

ORD record
ord-d59e36b0f42844ae84f8c0c8a63afe67
Source dataset
uspto-grants-1979_10
Patent number
US04172839

Reaction notes

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