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

HRID 848870Notes

Reaction equation

HRID 848870 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-ol

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 produce 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
  6. customto give 9.24 g
  7. customof produce as an oil

Sources & evidence

ORD record
ord-fd6c71575b58480782a04f50778eb0cc
Source dataset
uspto-grants-1981_10
Patent number
US04297516

Reaction notes

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