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

HRID 1389957Notes

Reaction equation

HRID 1389957 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
67 °C

Procedure

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-cyclohexenecaboxaldehyde 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).

Workup

  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

Sources & evidence

ORD record
ord-3a78c3e0a73e46038ca78903b96b7766
Source dataset
uspto-grants-1981_01
Patent number
US04247423

Reaction notes

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