Methyl iodide → 6-Methoxy-7sec. butoxy-2,2-dimethyl-4-chromanone

HRID 1607648Notes

Reaction equation

HRID 1607648 reaction equation
[OH-].[Na+].[CH3:3]I.[OH:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[O:16][CH:17]([CH2:19][CH3:20])[CH3:18])[O:12][C:11]([CH3:22])([CH3:21])[CH2:10][C:9]2=[O:23]>ClCCl.[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C>[CH3:3][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[O:16][CH:17]([CH2:19][CH3:20])[CH3:18])[O:12][C:11]([CH3:21])([CH3:22])[CH2:10][C:9]2=[O:23]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 143349736-Hydroxy-7-sec. butoxy-2,2-dimethyl-4-chromanone

Product 1

HCID 143349836-Methoxy-7sec. butoxy-2,2-dimethyl-4-chromanoneYield 96%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

In 40 ml of a 5% sodium hydroxide solution 5.2 g (20 millimoles) of 6-hydroxy-7-sec. butoxy-2,2-dimethyl-4-chromanone are dissolved whereupon 80 ml of dichloro methane and 0.5 g of triethyl benzyl ammonium chloride are added and the mixture is intensively stirred at room temperature for 30 minutes. After the addition of 4.25 g (1.9 ml, 30 millimoles) of methyl iodide the reaction mixture is stirred for further 2 hours. The organic phase is separated, washed twice with 50 ml of water each, dried over sodium sulfate and the solvent is removed. The residue is crystallized from 90% ethanol. Thus 5.34 g of the desired compound are obtained, yield 96%. Mp.: 92.5°-93° C.

Workup

  1. additionare added
  2. stirringis stirred for further 2 hours
  3. customThe organic phase is separated
  4. washwashed twice with 50 ml of water each,
  5. dry with materialdried over sodium sulfate
  6. customthe solvent is removed
  7. customThe residue is crystallized from 90% ethanol

Sources & evidence

ORD record
ord-e0e58543d92b4a5f92e41338cc72bfb4
Source dataset
uspto-grants-1989_09
Patent number
US04866089

Reaction notes

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