Dichloromethane → (5E)-2,6-Dimethyl-5,7-octadien-2-ol

HRID 463564Notes

Reaction equation

HRID 463564 reaction equation
OC/C(/C)=C/CC/C(/C)=C/CN(CC)CC.C(Cl)Cl.[CH3:20][C:21]([OH:30])([CH2:23][CH2:24][CH2:25][C:26]([CH:28]=[CH2:29])=[CH2:27])[CH3:22]>>[CH3:27]/[C:26](/[CH:28]=[CH2:29])=[CH:25]\[CH2:24][CH2:23][C:21]([OH:30])([CH3:20])[CH3:22]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 109752-Methyl-6-methylene-7-octen-2-olHCID 88654554HCID 88654554, compound

Product 1

HCID 5368785(5E)-2,6-Dimethyl-5,7-octadien-2-ol

Procedure

Into a 300-ml reactor equipped with a rectifying column (with an estimated number of theoretical plates of 10) filled with "Helipack" was charged 103 g (0.454 mol) of hydroxygeranyl diethylamine. The atmosphere was replaced with nitrogen. 33.6 ml (0.908 mmol) of the above-mentioned methylene chloride solution was added, and the reactants were heated under a reduced pressure of 1 mmHg. About 35 minutes after the reactant temperature in the flask had reached 150° C., distillation was started at a column top temperature of 63° C. After carrying out the reaction for 5 hours, a mixture of myrcenol and ocimenol was obtained in an amount of 59.4 g. The results from gas chromatography indicated that the mixture was composed of 87.6% of myrcenol and 12.4% of ocimenol.

Workup

  1. additionfilled with "Helipack"
  2. temperaturethe reactants were heated under a reduced pressure of 1 mmHg
  3. distillationdistillation
  4. customwas started at a column top temperature of 63° C
  5. customthe reaction for 5 hours

Sources & evidence

ORD record
ord-35d558ab6fe14a28bb4f3669c9d769b9
Source dataset
uspto-grants-1985_05
Patent number
US04520212

Reaction notes

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