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

HRID 262854Notes

Reaction equation

HRID 262854 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 prepared 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 coombined 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 coombined ether extracts are washed successively with ammonium chloride and water
  5. customdried

Sources & evidence

ORD record
ord-a5f3e247922144a7a1f0ae11003ffdae
Source dataset
uspto-grants-1979_05
Patent number
US04154959

Reaction notes

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