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

HRID 1155404Notes

Reaction equation

HRID 1155404 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-cyclohexenecarboxaldehyde at reflux (67° C.) over a two-year 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-50f6536ad0be45a4a0cf825f7115983d
Source dataset
uspto-grants-1981_11
Patent number
US04301309

Reaction notes

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