Dimethyl Sulfate → 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dimethoxy-2,2-dimethyl-

HRID 1073371Notes

Reaction equation

HRID 1073371 reaction equation
[CH2:1](C(C)=O)C.[OH:6][C:7]1[CH:16]=[C:15](O)[CH:14]=[C:13]2[C:8]=1C(=O)[CH2:10][C:11]([CH3:19])([CH3:18])[O:12]2.[C:21](=[O:24])([O-])[O-].[K+].[K+].S([O:32][CH3:33])(OC)(=O)=O>CC(C)=O>[CH3:1][O:6][C:7]1[CH:16]=[C:15]([O:32][CH3:33])[CH:14]=[C:13]2[C:8]=1[C:21](=[O:24])[CH2:10][C:11]([CH3:19])([CH3:18])[O:12]2

Participants

6

Reactant 4

HCID 6497Dimethyl SulfateHCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 8213625,7-Dihydroxy-2,2-dimethylchroman-4-one

Product 1

HCID 6021244H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dimethoxy-2,2-dimethyl-Yield 93.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In a mixture of 40 ml of acetone and 40 ml of methyl ethyl ketone 4.2 g (20 millimoles) of 5,7-dihydroxy-2,2-dimethyl-4-chromanone are dissolved, whereupon to the solution 8.3 g (60 millimoles) of potassium carbonate and 5.3 g (3.9 ml, 42 millimoles) of dimethyl sulfate are added under stirring. The reaction mixture is refluxed for 8 hours, the suspension is cooled under stirring, the precipitated inorganic salt is filtered off, washed twice with 20 ml of acetone each and the solvent is removed in vacuo. The residue is taken up in 100 ml of chloroform, washed subsequently with 50 ml of 2% sodium hydroxide solution and 50 ml of water, dried over sodium sulfate and the chloroform is removed in vacuo. The residue is crystallized from 70% ethanol. Thus 4.4 g of the desired compound are obtained, yield 93.1%. Mp.: 104°-105° C.

Workup

  1. additionare added
  2. temperatureThe reaction mixture is refluxed for 8 hours
  3. temperaturethe suspension is cooled
  4. stirringunder stirring
  5. filtrationthe precipitated inorganic salt is filtered off
  6. washwashed twice with 20 ml of acetone each and the solvent
  7. customis removed in vacuo
  8. washwashed subsequently with 50 ml of 2% sodium hydroxide solution and 50 ml of water
  9. dry with materialdried over sodium sulfate
  10. customthe chloroform is removed in vacuo
  11. customThe residue is crystallized from 70% ethanol

Sources & evidence

ORD record
ord-66b490fb1a234be789af41dc8af417a0
Source dataset
uspto-grants-1990_11
Patent number
US04968819

Reaction notes

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