Dimethyl Sulfate → HCID 54390956, compound

HRID 1721479Notes

Reaction equation

HRID 1721479 reaction equation
S(OC)(O[CH3:5])(=O)=O.[K].[OH:9][N:10]=[C:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][O:21][C:22]1[CH:27]=[C:26]([CH3:28])[CH:25]=[CH:24][C:23]=1[CH3:29])[C:12]#[N:13]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH3:5][O:9][N:10]=[C:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][O:21][C:22]1[CH:27]=[C:26]([CH3:28])[CH:25]=[CH:24][C:23]=1[CH3:29])[C:12]#[N:13]

Participants

6

Reactant 3

HCID 6497Dimethyl SulfateHCID 5462222PotassiumHCID 85405589HCID 85405589, compound

Product 1

HCID 54390956HCID 54390956, compoundYield 4.7%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

To a mixture of 924 g of toluene and 13.6 g (0.042 mol) of tetra-n-butylammonium bromide were simultaneously added dropwise 127 g (1.01 mol) of dimethyl sulfate and 1460 g of an aqueous solution containing 268 g (0.84 mol, E/Z=19/81) of the potassium salt of α-hydroxyimino-2-(2,5-dimethylphenoxymethyl)phenylacetonitrile produced in accordance with Example 3-(2) over 5 hours while keeping at 20°-25° C., and the reaction was subsequently allowed to proceed at the same temperature for 1.5 hours. The aqueous layer was removed from the reaction mixture by phase separation, and the organic layer was washed with 1000 g of 5% aqueous sodium hydroxide solution and then washed twice with 250 g of 10% saline solution. The organic layer was concentrated under reduced pressure and dried, which afforded 245 g of α-methoxyimino-2-(2,5-dimethylphenoxymethyl)phenylacetonitrile. The analysis by high performance liquid chromatography revealed that the content and yield of α-methoxyimino-2-(2,5-dimethylphenoxymethyl)phenylacetonitrile was 89.6% and 88.6% (E/Z=17/83), respectively, and the content and yield of the nitron compound as a by-product was 4.8% and 4.7% yield (E/Z=91/9), respectively.

Workup

  1. customproduced in accordance with Example 3-(2) over 5 hours
  2. customwhile keeping at 20°-25° C.
  3. customThe aqueous layer was removed from the reaction mixture by phase separation
  4. washthe organic layer was washed with 1000 g of 5% aqueous sodium hydroxide solution
  5. washwashed twice with 250 g of 10% saline solution
  6. concentrationThe organic layer was concentrated under reduced pressure
  7. customdried

Sources & evidence

ORD record
ord-06b6c646e7c04ba3a745d1060da6aafd
Source dataset
uspto-grants-1996_04
Patent number
US05510506

Reaction notes

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