Methyl iodide → HCID 21387529, compound

HRID 1833854Notes

Reaction equation

HRID 1833854 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[CH:4]([C:6]1[O:7][CH:8]=[CH:9][CH:10]=1)[OH:5].[H-].[Na+].[CH3:17]I>CN(C)C=O.C(OCC)C>[Cl:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[CH:4]([C:6]1[O:7][CH:8]=[CH:9][CH:10]=1)[O:5][CH3:17]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21387541HCID 21387541, compound

Product 1

HCID 21387529HCID 21387529, compoundYield 89.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A soluton of (±) 2-(2-chloro-α-hydroxybenzyl)furan [prepared as described in (j) above] (31.3 g.) in dimethylformamide (100 ml.) was treated with sodium hydride (4.1 g.) with ice cooling. Methyl iodide (28.4 g.) was added to the stirred solution over 15 minutes at 15°-30° C. with ice cooling and the mixture was allowed to stand at ambient temperature for 1 hour. The mixture was then diluted with diethyl ether (300 ml.) and filtered. The filtrate was washed with water (3 × 500 ml.), dried over sodium sulphate and evaporated to give a light red oil, which was distilled to give (±) 2-(2-chloro-α-methoxybenzyl)furan (30 g.), b.p. 115° C./0.1 mm.Hg.

Workup

  1. filtrationfiltered
  2. washThe filtrate was washed with water (3 × 500 ml.)
  3. dry with materialdried over sodium sulphate
  4. customevaporated
  5. customto give a light red oil, which
  6. distillationwas distilled

Sources & evidence

ORD record
ord-59f6cc15f22f47d584ed1c260b93e66d
Source dataset
uspto-grants-1978_01
Patent number
US04067723

Reaction notes

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