Triphenylphosphine → HCID 53960761, compound

HRID 1379916Notes

Reaction equation

HRID 1379916 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(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[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 11776TriphenylphosphineHCID 86751364HCID 86751364, compound

Product 1

HCID 53960761HCID 53960761, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

(S)-3,7-dimethyl-6-hydroxy-7-octene-1-ol (I) (10.0 g, 58.1 mmol), palladium acetate (130.0 mg, 0.579 mmol), and triphenylphosphine (1.52 g, 5.795 mmol) were placed in a 50 ml three neck distillation flask provided with a thermometer and a vacuum distilling apparatus having a side arm. Butanol (20 ml) was then added to the flask and the mixture was heated for 12 hours with stirring at a reaction temperature of 115° to 120° C. and a atmospheric pressure in a stream of nitrogen. After the reaction had terminated, the flask was evacuated to remove solvent from the reaction mixture, and the resultant was distilled to obtain 7.2 g (89° to 91° C./4 mmHg) of (S)-3,7-dimethyl-5,7-octadiene-1-ol (II). The yield was 80%.

Workup

  1. customprovided with a thermometer
  2. distillationa vacuum distilling apparatus
  3. additionButanol (20 ml) was then added to the flask
  4. temperaturethe mixture was heated for 12 hours
  5. customAfter the reaction had terminated
  6. customthe flask was evacuated
  7. customto remove solvent from the reaction mixture
  8. distillationthe resultant was distilled

Sources & evidence

ORD record
ord-4d8bca6730c948cc8bea4c883a82c1c7
Source dataset
uspto-grants-1997_09
Patent number
US05672783

Reaction notes

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