Dimethyl Sulfate → HCID 2825022, compound

HRID 1607629Notes

Reaction equation

HRID 1607629 reaction equation
[OH-].[Na+].S(OC)(O[CH3:7])(=O)=O.[OH:10][C:11]1[C:20]([CH3:21])=[C:19]2[C:14]([C:15](=[O:24])[CH2:16][C:17]([CH3:23])([CH3:22])[O:18]2)=[CH:13][CH:12]=1>O>[CH3:7][O:10][C:11]1[C:20]([CH3:21])=[C:19]2[C:14]([C:15](=[O:24])[CH2:16][C:17]([CH3:22])([CH3:23])[O:18]2)=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 27279747-Hydroxy-2,2,8-trimethyl-2,3-dihydro-4H-1-benzopyran-4-one

Product 1

HCID 2825022HCID 2825022, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The reaction is carried out under nitrogen. In 50 ml of a 10% sodium hydroxide solution 4.9 g (20 millimoles) of 7-hydroxy-2,2,8-trimethyl-4-chromanone are dissolved, 2.6 g (2 ml, 21 millimoles) of dimethyl sulfate are added and the reaction mixture is vigorously stirred for 2 hours. The reaction mixture is diluted with 100 ml of icecold water and extracted three times with 50 ml of carbon tetrachloride each. The organic phase is washed twice with 50 ml of water each, dried over sodium sulfate, the solvent is removed and the residue crystallized from 90% methanol. Thus 3.4 g of the desired compound are obtained, yield 78%. Mp.: 105°-107° C.

Workup

  1. extractionextracted three times with 50 ml of carbon tetrachloride each
  2. washThe organic phase is washed twice with 50 ml of water each,
  3. dry with materialdried over sodium sulfate
  4. customthe solvent is removed
  5. customthe residue crystallized from 90% methanol

Sources & evidence

ORD record
ord-a16aa53551be4eeab7c0b4b470865be7
Source dataset
uspto-grants-1989_09
Patent number
US04866089

Reaction notes

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