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

HRID 224245

반응식

HRID 224245 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 20561535alpha-Allyl-4-methyl-3-cyclohexene methanol수율 65.2%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
71 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-299bd4a4f5fd495f94abc7185a3fa17e
출처 데이터셋
uspto-grants-1980_11
특허 번호
US04231940

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