Allyl chloride → alpha-Allyl-4-methyl-3-cyclohexene methanol

HRID 444113

反応式

HRID 444113 の反応式
[CH2:1](Cl)[CH:2]=[CH2:3].[CH3:5][C:6]1[CH2:11][CH2:10][CH:9]([CH:12]=[O:13])[CH2:8][CH:7]=1.[Mg].O1CCCC1>C1(C)C=CC=CC=1>[CH2:3]([CH:12]([CH:9]1[CH2:10][CH2:11][C:6]([CH3:5])=[CH:7][CH2:8]1)[OH:13])[CH:2]=[CH2:1]

参加物

6

反応物 4

HCID 7850Allyl chlorideHCID 8028TetrahydrofuranHCID 1110123-Cyclohexene-1-carboxaldehyde, 4-methyl-HCID 5462224Magnesium

生成物 1

HCID 20561535alpha-Allyl-4-methyl-3-cyclohexene methanol収率 65.2%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
71 °C

実験手順

A solution of 251 grams (3.3 moles) of allyl chloride and 372 grams (3 moles) of 4-methyl-3-cyclohexenecarboxaldehyde is added dropwise to a stirred slurry of 77 grams of magnesium (3.2 moles) and 1500 ml of tetrahydrofuran at reflux under nitrogen over a three-hour period. The reaction mixture is heated at reflux (71° C.) for 30 minutes after the feed is complete, whereupon 500 ml of toluene is added. A distillation head is attached to the reaction flask and the tetrahydrofuran is distilled off at atmospheric pressure to a pot temperature of 100° C. The remaining organic solution is cooled to 0° C., whereupon 1000 ml of 18% hydrochloric acid solution is slowly added with external cooling. Two clear layers is formed. The aqueous layer is discarded and the organic layer is quickly distilled. The distillate is fractionally redistilled through a 1.5"×12" Goodloe packed column to afford 325 grams of alpha-allyl-4-methyl-3-cyclohexene methanol (b.p. 92° C., 3.0 mm Hg pressure).

後処理

  1. temperatureat reflux under nitrogen over a three-hour period
  2. temperatureThe reaction mixture is heated
  3. additionis added
  4. distillationthe tetrahydrofuran is distilled off at atmospheric pressure to a pot temperature of 100° C
  5. temperatureThe remaining organic solution is cooled to 0° C., whereupon 1000 ml of 18% hydrochloric acid solution
  6. additionis slowly added with external cooling
  7. customTwo clear layers is formed
  8. distillationthe organic layer is quickly distilled
  9. distillationThe distillate is fractionally redistilled through a 1.5"×12" Goodloe

出典と根拠

ORDレコード
ord-120aeb7e7f5346edac5e30bb1e7731ac
出典データセット
uspto-grants-1981_04
特許番号
US04263149

関連ノート

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