Dimethyl Sulfate → HCID 14592976, compound

HRID 1073394Notes

Reaction equation

HRID 1073394 reaction equation
[CH2:1]([O:5][C:6]1[C:15]([OH:16])=[C:14]2[C:9]([C:10](=[O:19])[CH2:11][C:12]([CH3:18])([CH3:17])[O:13]2)=[CH:8][CH:7]=1)[CH:2]([CH3:4])[CH3:3].S(OC)(O[CH3:24])(=O)=O>[OH-].[Na+]>[CH2:1]([O:5][C:6]1[C:15]([O:16][CH3:24])=[C:14]2[C:9]([C:10](=[O:19])[CH2:11][C:12]([CH3:17])([CH3:18])[O:13]2)=[CH:8][CH:7]=1)[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 14592966HCID 14592966, compound

Product 1

HCID 14592976HCID 14592976, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
50 °C

Procedure

In 50 ml of a 10% sodium hydroxide solution under nitrogen 5.2 g (20 millimoles) of 7-isobutoxy-8-hydroxy-2,2,-dimethyl-4-chromanone are dissolved, whereupon 2.6 g (2 ml, 21 millimoles) of dimethyl sulfate are added and the reaction mixture is intensively stirred for 3 hours at 50° C. The mixture is diluted with 100 ml of ice cold water, extracted three times with 50 ml of chloroform each, the organic phase is washed twice with 40 ml of water dried over sodium sulfate and the solvent is evaporated. Thus 5.2 g of the desired compound are obtained in the form of yellow oil, yield 93%.

Workup

  1. additionare added
  2. extractionextracted three times with 50 ml of chloroform each, the organic phase
  3. washis washed twice with 40 ml of water
  4. dry with materialdried over sodium sulfate
  5. customthe solvent is evaporated

Sources & evidence

ORD record
ord-b505c0e4289543c3b7570d9a4509304a
Source dataset
uspto-grants-1990_11
Patent number
US04968819

Reaction notes

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