Hydrochloric Acid → (5-Iodo-3-methyl-pentyl)-benzene

HRID 749047Notes

Reaction equation

HRID 749047 reaction equation
[CH3:1][CH:2]([CH2:11][CH2:12]O)[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CC=CC=1.[I:39]I.Cl>ClCCl>[I:39][CH2:12][CH2:11][CH:2]([CH3:1])[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 807IodineHCID 1049PyridineHCID 11776TriphenylphosphineHCID 108312Phenylisohexanol

Product 1

HCID 91062273(5-Iodo-3-methyl-pentyl)-benzeneYield 210.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5 g (28 mmol) Phenoxanol (3-Methyl-5-phenyl-pentan-1-ol) is dissolved in 200 ml dichloromethane under nitrogen and stirring. Triphenylphosphine (8.8 g, 34 mmol) and 4.2 g (53 mmol) pyridine are added at 25° C. After cooling to 0° C. iodine (8.5 g, 34 mmol) is added. After 2 h stirring at 0° C. the reaction mixture is poured on ice-cooled 1 N HCl and extracted with dichloromethane. The combined organic phases are washed with 10% Na2S2O3, sat. NaHCO3 and sat. NaCl. Drying over MgSO4 and evaporation gives 17 g of a residue which is triturated with hexane and filtered over a 5 cm Silicagel pad. The filtrate is evaporated under reduced pressure and dried under high vacuum giving 7.1 g of 7c as a colorless oil.

Workup

  1. additionis added
  2. stirringAfter 2 h stirring at 0° C. the reaction mixture
  3. additionis poured on ice-
  4. extractionextracted with dichloromethane
  5. washThe combined organic phases are washed with 10% Na2S2O3, sat. NaHCO3 and sat. NaCl
  6. dry with materialDrying over MgSO4 and evaporation

Sources & evidence

ORD record
ord-7d291f58b1f04244a37bb1ab31406759
Source dataset
uspto-grants-2008_07
Patent number
US07402576B2

Reaction notes

Loading…