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

HRID 1449271Notes

Reaction equation

HRID 1449271 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 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-d1f99aba59194f72b5d7aa87be24cc4f
Source dataset
uspto-grants-1980_02
Patent number
US04189597

Reaction notes

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