Carbon Tetrachloride → 1-(Chloromethyl)-4-propylbenzene

HRID 914479Notes

Reaction equation

HRID 914479 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10]O)=[CH:6][CH:5]=1)[CH2:2][CH3:3].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:32]>>[Cl:32][CH2:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:1][CH2:2][CH3:3])=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 2760472(4-Propylphenyl)methanol

Product 1

HCID 122531731-(Chloromethyl)-4-propylbenzene

Procedure

(4-Propylphenyl)methanol (4.93 g) synthesized in Reference Example 36 was dissolved in carbon tetrachloride (65 mL), triphenylphosphine (9.5 g) was added thereto, and the mixture was heated under reflux for 4 hr. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in hexane. The insoluble material was filtered off, and the filtrate was evaporated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent; hexane) to give the title compound (2.24 g) as a colorless oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in hexane
  5. filtrationThe insoluble material was filtered off
  6. customthe filtrate was evaporated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (elution solvent; hexane)

Sources & evidence

ORD record
ord-11ab0712b6b94be5bfe5a295786ff946
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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