Hydrochloric Acid → 9H-xanthene-3,6-diol

HRID 54715

反応式

HRID 54715 の反応式
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=O)[C:7]3[C:12]([O:13][C:14]=2[CH:15]=1)=[CH:11][C:10]([OH:16])=[CH:9][CH:8]=3.B#B.O.Cl>C1COCC1>[CH2:6]1[C:5]2[CH:4]=[CH:3][C:2]([OH:1])=[CH:15][C:14]=2[O:13][C:12]2[CH:11]=[C:10]([OH:16])[CH:9]=[CH:8][C:7]1=2

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 57493223,6-dihydroxy-9H-xanthen-9-oneHCID 6328200Diboron

生成物 1

HCID 99908139H-xanthene-3,6-diol収率 93.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a suspension of 3,6-dihydroxyxanthone (46 g, 201 mmol.) obtained as in Example 1 in 1.6 L of THF was added over 1 hr 800 ml of borane-tetrahydrofuran complex (1.0M in THF, caution very vigorous raction at beginning). This mixture was stirred overnight under argon at room temperature to give a clear yellow solution. The excess diborane was decomposed by careful addition of water followed by 1N HCl to give a clear yellow solution. The tetrahydrofuran was removed by rotary evaporation and the resulting solid filtered, washed with water and redissolved in 10% NaOH. This solution was filtered, cooled and reprecipitated with slow addition of HCl to give a yellow solid which was filtered, washed with water and dried under vacuum to give 40.14 g (93%, mp 207-208) of 3,6-Dihydroxyxanthane. H1NMR (DMSO): 9.41 (s, 2H); 6.97 (d, 2H, J=8.4 Hz), 6.4 (dd, 2H, J=8.4, 2.4 Hz), 6.39 (d, 2H, J=2.4 Hz), 3.765 (s, 2H).

後処理

  1. customto give a clear yellow solution
  2. customto give a clear yellow solution
  3. customThe tetrahydrofuran was removed by rotary evaporation
  4. filtrationthe resulting solid filtered
  5. washwashed with water
  6. dissolutionredissolved in 10% NaOH
  7. filtrationThis solution was filtered
  8. temperaturecooled
  9. customreprecipitated with slow addition of HCl
  10. customto give a yellow solid which
  11. filtrationwas filtered
  12. washwashed with water
  13. customdried under vacuum

出典と根拠

ORDレコード
ord-de19ba1425fd497caef939f199f20c27
出典データセット
uspto-grants-1997_04
特許番号
US05623080

関連ノート

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