Pentane → Benzene, (3-methyl-3-buten-1-ynyl)-

HRID 369442Notes

Reaction equation

HRID 369442 reaction equation
[CH3:1][C:2]([CH:4](O)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[CH2:3].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCCCC>O1CCCC1.C(Cl)(Cl)(Cl)Cl>[CH3:3][C:2]([C:4]#[C:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[CH2:1]

Participants

6

Reactant 3

HCID 8003PentaneHCID 11776TriphenylphosphineHCID 12642434HCID 12642434, compound

Product 1

HCID 10975591Benzene, (3-methyl-3-buten-1-ynyl)-

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 100 mmol of 2-methyl-4-phenylbut-1-en-3-ol (16.02 g) in 90 mL of tetrahydrofuran and 210 mL of carbon tetrachloride was mixed with 300 mmol (78.70 g) of dry triphenylphosphine. The solution was heated to boiling under reflux for 2 hours, whereupon a precipitate formed. After cooling, 400 mL of pentane was added and the precipitate was separated by filtration. The solvent was removed from the filtrate under reduced pressure and the residue was fractionally distilled to give 2-methyl-4-phenylbut-1-en-3-yne havng the formula: ##STR27##

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux for 2 hours, whereupon a precipitate
  3. customformed
  4. temperatureAfter cooling
  5. customthe precipitate was separated by filtration
  6. customThe solvent was removed from the filtrate under reduced pressure
  7. distillationthe residue was fractionally distilled

Sources & evidence

ORD record
ord-85373a38077f4b0893a500addc8f35e1
Source dataset
uspto-grants-2000_10
Patent number
US06136940

Reaction notes

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