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

HRID 1155249노트

반응식

HRID 1155249 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
67 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-565e404aeb4644c4adebdc10d0a52549
출처 데이터셋
uspto-grants-1981_11
특허 번호
US04301018

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