Dimethyl Sulfate → 6-Hydroxy-3-methoxyxanthone

HRID 2399641ノート

反応式

HRID 2399641 の反応式
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:17])[C:7]3[C:12]([O:13][C:14]=2[CH:15]=1)=[CH:11][C:10]([OH:16])=[CH:9][CH:8]=3.[CH3:18]OS(OC)(=O)=O>O.C(O)C>[OH:16][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[C:6](=[O:17])[C:5]1[CH:4]=[CH:3][C:2]([O:1][CH3:18])=[CH:15][C:14]=1[O:13]2

参加物

5

反応物 2

HCID 6497Dimethyl SulfateHCID 57493223,6-dihydroxy-9H-xanthen-9-one

生成物 1

HCID 124481156-Hydroxy-3-methoxyxanthone収率 50%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

7.0 g (30.7 mmol) of 3,6-dihydroxyxanthone is dissolved in aq. NAOH (2.5 g(62.5 mmol) in 200 mls H2O). 3.2 mls (33.6 mmol) of dimethylsulfate is added dropwise with stirring, and solid forms immediately upon completion. Stirred further 1 hour and heated to reflux for 15 minutes. Additional base is added to insure complete solubility of phenols. The solution is acidified with HCl, and filtration yields a mixture of staring material and the target compound. Solid is heated to reflux in about 200 mls ethanol for 15 minutes to dissolve starting material, and solid is filtered out, washing with ethanol and water. This may have to be repeated several times to obtain pure compound in about 50% yield; mp=303-306-C.NMR (200 MHZ in d-DMSO) s 3.89 (3H,s), 6.82 (1H,d,J=2.24 Hz), 6.87 (1H,m), 6.99 (1H,dd,J=8.78 Hz, 2.20 Hz),, 7.09 (1H,d,J=2.26Hz), 7.99 (1H,d,J=8.52 Hz), 8.03 (1H,d,J=8.78Hz).

後処理

  1. stirringStirred further 1 hour
  2. temperatureheated
  3. temperatureto reflux for 15 minutes
  4. additionAdditional base is added
  5. filtrationThe solution is acidified with HCl, and filtration
  6. customyields
  7. additiona mixture of staring material
  8. temperatureSolid is heated
  9. dissolutionto dissolve
  10. filtrationis filtered out
  11. washwashing with ethanol and water
  12. customto obtain pure compound in about 50% yield

出典と根拠

ORDレコード
ord-8ac3d9ff94c44661a538a512c388a7c8
出典データセット
uspto-grants-1995_09
特許番号
US05451343

反応ノート

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