Methyl iodide → HCID 14626976, compound

HRID 1608133Notes

Reaction equation

HRID 1608133 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:14][CH2:15][C:16]#[CH:17])[C:9]=1[O:10][CH2:11][C:12]#[CH:13])[CH2:5][OH:6].[OH-].[K+].I[CH3:21]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:5][O:6][CH3:21])[CH:7]=[C:8]([O:14][CH2:15][C:16]#[CH:17])[C:9]=1[O:10][CH2:11][C:12]#[CH:13]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 14130328{3-Chloro-4,5-bis[(prop-2-yn-1-yl)oxy]phenyl}methanol

Product 1

HCID 14626976HCID 14626976, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-chloro-4,5-dipropargyloxybenzyl alcohol (1.00 g), potassium hydroxide (1.00 g), iodomethane (1.00 g) and tetra-n-butylammonium bromide (1.00 g) in tetrahydrofuran (30 ml) was stirred at room temperature for 2 hours, poured into ice-water and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography using toluene as an eluent to give 1-chloro-5-methoxymethyl-2,3-dipropargyloxybenzene (0.95 g). nD23.0 1.5450.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a2c223d4e15b49158bd94958e54fead4
Source dataset
uspto-grants-1989_09
Patent number
US04870064

Reaction notes

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