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

HRID 1073392Notes

Reaction equation

HRID 1073392 reaction equation
[CH3:1]I.[OH:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH:15]([CH2:17][CH3:18])[CH3:16])[O:10][C:9]([CH3:20])([CH3:19])[CH2:8][C:7]2=[O:21]>[OH-].[Na+].ClCCl.[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C>[CH3:1][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH:15]([CH2:17][CH3:18])[CH3:16])[O:10][C:9]([CH3:19])([CH3:20])[CH2:8][C:7]2=[O:21]

Participants

6

Reactant 2

HCID 6328Methyl iodideHCID 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 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

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 another 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 another 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-d54b739894a9434aa1b91c8f82b0df2c
Source dataset
uspto-grants-1990_11
Patent number
US04968819

Reaction notes

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