1,6,10-Dodecatrien-3-ol, 3,7,11-trimethyl-, [S-(Z)]- → Nerolidol

HRID 2419267Notes

Reaction equation

HRID 2419267 reaction equation
[CH3:1][C:2]([CH3:16])=[CH:3][CH2:4][CH2:5]/[C:6](/[CH3:15])=[CH:7]\[CH2:8][CH2:9][C:10]([OH:14])([CH:12]=[CH2:13])[CH3:11]>C(Cl)(Cl)(Cl)Cl>[CH3:1][C:2]([CH3:16])=[CH:3][CH2:4][CH2:5]/[C:6](/[CH3:15])=[CH:7]/[CH2:8][CH2:9][C:10]([OH:14])([CH:12]=[CH2:13])[CH3:11]

Participants

3

Reactant 1

HCID 53201281,6,10-Dodecatrien-3-ol, 3,7,11-trimethyl-, [S-(Z)]-

Product 1

HCID 5284507Nerolidol

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Next, 1,000 g. of a mixture of cis- and trans-nerolidol in a ratio of 40:60 were rectified using a rectifying column having about 40 theoretical plates at 135° - 140° C. of the column bottom temperature at 0.3 - 0.5 mmHg of reduced pressure under reflux ratio of 10 to obtain 183 g. of cis-nerolidol (0.3 mmHg). This yield was 46 percent of distillation yield for cis-isomer charged. Its refractive index was nD30 = 1.4753 and its NMR spectrum in carbon tetrachloride is shown in FIG. 4. 324 g. of trans-nerolidol were obtained from the distillate having b.p. 107° - 110° C. (0.5 mmHg). This was 54 percent of distillation yield for trans-isomer charged. Its refractive index was nD30 = 1.4754 and its NMR spectrum is shown in FIG. 6. 477 g. of intermediate distillate in a ratio of 46:54 of cis- : trans-isomer were also obtained.

Workup

  1. customat 135° - 140° C.
  2. customto obtain 183 g
  3. distillationThis yield was 46 percent of distillation
  4. customyield for cis-isomer
  5. additioncharged

Sources & evidence

ORD record
ord-0ab77e1ab873454ea42d84d582fbec91
Source dataset
uspto-grants-1978_08
Patent number
US04105700

Reaction notes

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