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

HRID 444113

Reaction equation

HRID 444113 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
71 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-120aeb7e7f5346edac5e30bb1e7731ac
Source dataset
uspto-grants-1981_04
Patent number
US04263149

Linked notes

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