Methyl iodide → HCID 2825021, compound

HRID 1607628Notes

Reaction equation

HRID 1607628 reaction equation
[C:1](#N)C.C1OCCOCCOCCOCCOCCOC1.CI.[OH:24][C:25]1[CH:34]=[C:33]2[C:28]([C:29](=[O:37])[CH2:30][C:31]([CH3:36])([CH3:35])[O:32]2)=[C:27]([CH3:38])[CH:26]=1>[K]>[CH3:1][O:24][C:25]1[CH:34]=[C:33]2[C:28]([C:29](=[O:37])[CH2:30][C:31]([CH3:35])([CH3:36])[O:32]2)=[C:27]([CH3:38])[CH:26]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6342AcetonitrileHCID 2855718-Crown-6HCID 27279647-Hydroxy-2,2,5-trimethyl-2,3-dihydro-4H-1-benzopyran-4-one

Product 1

HCID 2825021HCID 2825021, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 5462222PotassiumSolvent

Procedure

In 50 ml of acetonitrile 4.9 g (20 millimoles) of the potassium salt of 7-hydroxy-2,2,5-trimethyl-4-chromanone are dissolved and the solution is stirred in the presence of 0.5 g (2 millimoles) of 18-Crown-6 at room temperature for 30 minutes. To the mixture 4.25 g (1.9 ml, 30 millimoles) of methyl iodide are added and the reaction mixture is stirred for a further hour. The inorganic salt is filtered off and the solvent is removed. The residue is taken up in chloroform, washed twice with 50 ml of water each, dried over sodium sulfate and evaporated. The product is crystallized from 90% ethanol. Thus 3.75 g of the desired compound are obtained, yield 85%. Mp.: 86°-88° C.

Workup

  1. filtrationThe inorganic salt is filtered off
  2. customthe solvent is removed
  3. washwashed twice with 50 ml of water each,
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe product is crystallized from 90% ethanol

Sources & evidence

ORD record
ord-d1b2ae970e3647928d1873f68bec5d4d
Source dataset
uspto-grants-1989_09
Patent number
US04866089

Reaction notes

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