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Hydrochloric Acid → 2-Methoxy-6-(4-propylcyclohexenyl)naphthalene

HRID 857588
ノート
印刷プレビュー

反応式

HRID 857588 の反応式
[Mg].Br[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=O)[CH:8]([O:14][CH3:15])[CH:7]=[CH:6]2.[CH2:16]([CH:19]1[CH2:24][CH2:23][CH:22]=[CH:21][CH2:20]1)[CH2:17][CH3:18].Cl>O1CCCC1>[CH3:15][O:14][C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([C:22]3[CH2:23][CH2:24][CH:19]([CH2:16][CH2:17][CH3:18])[CH2:20][CH:21]=3)[CH:4]=2)[CH:9]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 518777Cyclohexene, 4-propyl-HCID 5462224MagnesiumHCID 696505096-Bromo-2-methoxynaphthalone

生成物 1

HCID 218693902-Methoxy-6-(4-propylcyclohexenyl)naphthalene収率 80.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒
4 回

実験手順

5.7 g of magnesium was suspended in 12 ml of tetrahydrofuran. To the suspension was then added dropwise a solution of 50 g of 6-bromo-2-methoxynaphthalone in 200 ml of tetrahydrofuran at a rate such that tetrahydrofuran was gently refluxed. The reaction mixture was then further stirred for 1 hour. To the reaction solution was then added dropwise a solution of 30 g of 4-propylcyclohexanene in 120 ml of tetrahydrofuran at room temperature. The reaction mixture was then further stirred for 1 hour. To the reaction solution was then added 200 ml of a 10% hydrochloric acid. The reaction mixture was extracted with 300 ml of toluene, washed with water, saturated aqueous solution of sodium bicarbonate and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was then distilled off. To the residue were then added 280 ml of toluene and 4.0 g of p-toluenesulfonic acid monohydrate. The reaction mixture was then heated under reflux for 3 hours. The reaction solution was allowed to cool to room temperature, washed with water, saturated aqueous solution of sodium bicarbonate and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was then distilled off. The residue was then recrystallized from ethanol to obtain 44.8 g of 2-methoxy-6-(4-propylcyclohexa-1-ene-1-yl)naphthalene.

後処理

  1. temperaturewas gently refluxed
  2. stirringThe reaction mixture was then further stirred for 1 hour
  3. extractionThe reaction mixture was extracted with 300 ml of toluene
  4. washwashed with water, saturated aqueous solution of sodium bicarbonate and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was then distilled off
  7. additionTo the residue were then added 280 ml of toluene and 4.0 g of p-toluenesulfonic acid monohydrate
  8. temperatureThe reaction mixture was then heated
  9. temperatureunder reflux for 3 hours
  10. washwashed with water, saturated aqueous solution of sodium bicarbonate and saturated brine
  11. dry with materialdried over anhydrous sodium sulfate
  12. distillationThe solvent was then distilled off
  13. customThe residue was then recrystallized from ethanol

出典と根拠

ORDレコード
ord-439029414fd94f88ba06c922bc612387
出典データセット
uspto-grants-2006_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07145047B2

反応ノート

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