Allyl chloride → 1-(4,6-Dimethylcyclohex-3-en-1-yl)but-3-en-1-ol

HRID 444112ノート

反応式

HRID 444112 の反応式
[Mg].O1C[CH2:5][CH2:4][CH2:3]1.C(Cl)C=C.[CH3:11][C:12]1[CH2:17][CH:16]([CH3:18])[CH:15]([CH:19]=[O:20])[CH2:14][CH:13]=1>C1(C)C=CC=CC=1>[CH3:11][C:12]1[CH2:17][CH:16]([CH3:18])[CH:15]([CH:19]([CH2:5][CH:4]=[CH2:3])[OH:20])[CH2:14][CH:13]=1

参加物

6

反応物 4

HCID 7850Allyl chlorideHCID 8028TetrahydrofuranHCID 30158514,6-Dimethyl-3-cyclohexene-1-carboxaldehydeHCID 5462224Magnesium

生成物 1

HCID 205615391-(4,6-Dimethylcyclohex-3-en-1-yl)but-3-en-1-ol

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
67 °C

実験手順

To a stirred slurry of 53 grams of magnesium (2.2 mole) and 500 ml of dry tetrahydrofuran, under nitrogen, is dropwise added a solution of 168 grams (2.2 moles) of allyl chloride and 276 grams (2.0 moles) of 4,6-dimethyl-3-cyclohexenecarboxaldehyde at reflux (67° C.) over a two-hour period. The reaction mixture is heated to reflux for 30 minutes, whereupon 400 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 114° C. The remaining solution is cooled to 0° C., whereupon 900 ml of 18% hydrochloric acid solution is slowly added with external cooling. Two clear layers are formed. The aqueous layer is discarded and the organic layer is quickly distilled. The distillate is fractionally redistilled through a 1"×12" Goodloe packed column to afford 250 grams of 4,6-dimethyl-alpha-allyl-3-cyclohexenemethanol (b.p. 88°, 2.0 mm Hg pressure).

後処理

  1. temperatureThe reaction mixture is heated
  2. additionis added
  3. distillationthe tetrahydrofuran is distilled off at atmospheric pressure to a pot temperature of 114° C
  4. temperatureThe remaining solution is cooled to 0° C., whereupon 900 ml of 18% hydrochloric acid solution
  5. additionis slowly added with external cooling
  6. customTwo clear layers are formed
  7. distillationthe organic layer is quickly distilled
  8. distillationThe distillate is fractionally redistilled through a 1"×12" Goodloe

出典と根拠

ORDレコード
ord-7be008afba7b40f5ba2852fe3212e101
出典データセット
uspto-grants-1981_04
特許番号
US04263149

反応ノート

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