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

HRID 1155256Notes

Reaction equation

HRID 1155256 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
0 °C

Procedure

To a stirred slurry of 53 grams of magnesium (2.2 mole) and 500 ml of dry tetrahydrofuran under nitrogen, is added dropwise 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 over a two-hour period. The reaction mixture is heated at reflux for 30 minutes, whereupon 400 ml of toluene is added. A distillation head is attached to the reaction flask and the toluene is distilled at atmospheric pressure to a pot temperature of 114° C. The remaining solution is cooled to 0° C., whereupon 900 ml of 18% aqueous hydrochloric acid solution is slowly added with external cooling. Two clear layers are formed. The aqueous layer is discarded and the organic layer is washed twice with water, neutralizing the second wash with caustic soda. 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. 102°, 3.2 mm Hg pressure).

Workup

  1. temperatureat reflux over a two-hour period
  2. temperatureThe reaction mixture is heated
  3. additionis added
  4. distillationthe toluene is distilled at atmospheric pressure to a pot temperature of 114° C
  5. additionis slowly added with external cooling
  6. customTwo clear layers are formed
  7. washthe organic layer is washed twice with water
  8. washsecond wash with caustic soda
  9. distillationThe organic layer is quickly distilled
  10. distillationThe distillate is fractionally redistilled through a 1"×12" Goodloe

Sources & evidence

ORD record
ord-331c9ca272e54209bd354b4431f28ec7
Source dataset
uspto-grants-1981_11
Patent number
US04301024

Reaction notes

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