1,8-Dichloroanthraquinone → 1,8-Dimethoxyanthraquinone

HRID 344996

反応式

HRID 344996 の反応式
[O:1]1[CH2:5]CCC1.Cl[C:7]1[C:20]2[C:19](=[O:21])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3Cl)[C:12](=[O:23])[C:11]=2[CH:10]=[CH:9][CH:8]=1.C1OCCOCCOCCOCCOCC[O:26][CH2:25]1.C[O-].[Na+]>CO.CCOC(C)=O.C1(C)C=CC=CC=1>[CH3:25][O:26][C:7]1[C:20]2[C:19](=[O:21])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[O:1][CH3:5])[C:12](=[O:23])[C:11]=2[CH:10]=[CH:9][CH:8]=1

参加物

7

反応物 4

HCID 67081,8-DichloroanthraquinoneHCID 8028TetrahydrofuranHCID 2855718-Crown-6HCID 10942334Sodium Methoxide

生成物 1

HCID 808271,8-Dimethoxyanthraquinone収率 50%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 21584019Toluene ethylacetate溶媒

実験手順

A 5-liter round-bottom flask equipped with an overhead stirrer, thermocouple, and reflux condenser with a nitrogen/vacuum outlet was charged with 1200 mL of tetrahydrofuran, 138.5 grams of 1,8-dichloroanthraquinone, and 35.6 grams of 18-crown-6. This solution was deoxygenated, stirred under nitrogen, and heated until a clear solution was obtained. A solution of 165.0 grams of sodium methoxide in 1000 mL of methanol (prepared from sodium metal) was then added over a period of 30 min. The reaction mixture was heated at reflux for 24 hours, at which time TLC (silica gel, 1:1 EtOAc/toluene) indicated that the reaction was complete. The reaction was cooled overnight in an ice bath and the crystallized product isolated by filtration (82% crude yield). This material was recrystallized from 1000 mL of toluene to afford 1,8-dimethoxyanthraquinone in an overall yield of 50%.

後処理

  1. customA 5-liter round-bottom flask equipped with an overhead stirrer
  2. temperaturethermocouple, and reflux condenser with a nitrogen/vacuum outlet
  3. customThis solution was deoxygenated
  4. temperatureheated until a clear solution
  5. customwas obtained
  6. temperatureThe reaction mixture was heated
  7. temperatureThe reaction was cooled overnight in an ice bath
  8. customthe crystallized product isolated by filtration (82% crude yield)
  9. customThis material was recrystallized from 1000 mL of toluene

出典と根拠

ORDレコード
ord-05caa58bcd8247bdb6498d923ee4f120
出典データセット
uspto-grants-1991_10
特許番号
US05055439

関連ノート

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