1,1′-(1,4-Butanediyl)bis[1-phenylphosphine] → HCID 53960761, compound

HRID 1379917Notes

Reaction equation

HRID 1379917 reaction equation
[CH3:1][C@@H:2]([CH2:6][CH2:7][CH:8](O)[C:9]([CH3:11])=[CH2:10])[CH2:3][CH2:4][OH:5].C1(PCCCCPC2C=CC=CC=2)C=CC=CC=1>[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][C@@H:2]([CH2:6][CH:7]=[CH:8][C:9]([CH3:11])=[CH2:10])[CH2:3][CH2:4][OH:5]

Participants

4

Reactant 2

HCID 166877121,1′-(1,4-Butanediyl)bis[1-phenylphosphine]HCID 86751364HCID 86751364, compound

Product 1

HCID 53960761HCID 53960761, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalyst

Conditions

Temperature
150 °C

Procedure

(S)-3,7-dimethyl-6-hydroxy-7-octene-1-ol (I) (10.0 g, 58.1 mmol), bis(triphenylphosphine) palladium chloride (40.8 mg, 0.058 mmol), and 1,4-bisphenylphosphinobutane (1.24 g, 2.91 mmol) were placed in a 50 ml three neck distillation flask provided with a thermometer and a vacuum distilling apparatus having a side arm. The mixture was then heated for 6 hours with stirring at a reaction temperature of 150° C. under a reduced pressure of 25 mmHg while distilling dienes which is to be produced. 7.3 g (115° to 120° C./25 mmHg) of (S)-3,7-dimethyl-5,7-octadiene-1-ol (II) was obtained in 82% yield.

Workup

  1. customprovided with a thermometer
  2. distillationa vacuum distilling apparatus
  3. temperatureThe mixture was then heated for 6 hours
  4. distillationwhile distilling dienes which
  5. customto be produced

Sources & evidence

ORD record
ord-29ccadfcd6a7401a9e5b97216b9481f7
Source dataset
uspto-grants-1997_09
Patent number
US05672783

Reaction notes

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