Acetic Acid → 2,9-Dimethylpentacene

HRID 488950

反応式

HRID 488950 の反応式
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:6][C:7]3[C:20]([C:21](=O)[C:22]=2[CH:23]=1)=[CH:19][C:18]1[CH2:17][C:16]2[C:11](=[CH:12][C:13]([CH3:25])=[CH:14][CH:15]=2)[C:10](=O)[C:9]=1[CH:8]=3.CO.C(O)(=O)C.Cl>COCCOCCOC.O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[C:22](=[CH:21][C:20]3[C:7]([CH:6]=2)=[CH:8][C:9]2[C:18](=[CH:17][C:16]4[C:11]([CH:10]=2)=[CH:12][C:13]([CH3:25])=[CH:14][CH:15]=4)[CH:19]=3)[CH:23]=1

参加物

7

反応物 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 887MethanolHCID 114505987,14-Dihydro-3,10-dimethylpentacene-5,12-dione

生成物 1

HCID 114609502,9-Dimethylpentacene

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8150Diglyme溶媒

反応条件

温度
60 °C

実験手順

A mixture of 24.6 grams of 7,14-dihydro-3,10-dimethylpentacene-5,12-dione in 250 mL of 2-methoxyethyl ether was stirred and flushed with nitrogen for 10 minutes. To this was added in small portions 16.5 grams of sodium borohydride and stirring was continued at room temperature overnight. To the resulting reaction mixture was added slowly over 30 minutes 155 mL of methanol with the temperature maintained below 0° C. The mixture was stirred for 1.5 hours at room temperature. To the mixture was added slowly 360 mL of glacial acetic acid over 10 minutes. The resulting mixture was heated to 60° C. for 1.5 hours. To the mixture was added 100 mL of concentrated hydrochloric acid. The resulting mixture was heated for one hour and cooled to room temperature. To the mixture was added 250 mL of water and stirring was continued for five minutes. The resulting solid was collected by filtration and washed sequentially with 3 L of water, and 1 L of acetone, 1 L of tetrahydrofuran, and 1 L of acetone and dried to give 2,9-dimethylpentacene.

後処理

  1. customflushed with nitrogen for 10 minutes
  2. additionTo this was added in small portions 16.5 grams of sodium borohydride
  3. stirringstirring
  4. customTo the resulting reaction mixture
  5. temperaturemaintained below 0° C
  6. stirringThe mixture was stirred for 1.5 hours at room temperature
  7. temperatureThe resulting mixture was heated for one hour
  8. temperaturecooled to room temperature
  9. stirringstirring
  10. waitwas continued for five minutes
  11. filtrationThe resulting solid was collected by filtration
  12. washwashed sequentially with 3 L of water, and 1 L of acetone, 1 L of tetrahydrofuran, and 1 L of acetone
  13. customdried

出典と根拠

ORDレコード
ord-5baa06ca0ba3459d9e04cedf7e8f1c44
出典データセット
uspto-grants-2005_12
特許番号
US06974877B2

関連ノート

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