2-Methoxypropene → 5-hexyl-3,4-dihydro-2-methoxy-2-methyl-2H-pyran

HRID 487861

Reaction equation

HRID 487861 reaction equation
[CH2:1]([C:7](=[CH2:10])[CH:8]=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH3:11][O:12][C:13]([CH3:15])=[CH2:14]>[I-].[Zn+2].[I-]>[CH2:1]([C:7]1[CH2:10][CH2:14][C:13]([O:12][CH3:11])([CH3:15])[O:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 83002-MethoxypropeneHCID 112057952-Methylene-octanal

Product 1

HCID 190913095-hexyl-3,4-dihydro-2-methoxy-2-methyl-2H-pyranYield 15.4%

Reagents, catalysts & solvents 1

HCID 9883512zinc(II)iodideCatalyst

Procedure

To a zinc iodide suspension (0.21 g, 0.671 mmol) in 42 g (0.3 mol) of 2-hexyl-2-propenal there were added dropwise, at 60° C. and under nitrogen, 18.5 g (0.25 mol) of 2-methoxypropene. Once the introduction was completed (23 min), the reaction was allowed to continue for 6 h at 60° C. and the mixture was then distilled on a Vigreux column to give 8.16 g of 5-hexyl-3,4-dihydro-2-methoxy-2-methyl-2H-pyran (B.p. 73°-74°/3 Pa; yield 15.4%).

Workup

  1. custom(23 min)
  2. distillationthe mixture was then distilled on a Vigreux column

Sources & evidence

ORD record
ord-917135c6a9e140199e55bd47ff3e642d
Source dataset
uspto-grants-1994_03
Patent number
US05298486

Linked notes

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