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

HRID 1073371노트

반응식

HRID 1073371 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-66b490fb1a234be789af41dc8af417a0
출처 데이터셋
uspto-grants-1990_11
특허 번호
US04968819

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