Carbon Tetrachloride → 3-Phenoxybenzyl chloride

HRID 1927260Notes

Reaction equation

HRID 1927260 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH2:14]O)[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:36]>>[Cl:36][CH2:14][C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:9]=1

Participants

4

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 262953-Phenoxybenzyl alcohol

Product 1

HCID 932913-Phenoxybenzyl chloride

Procedure

To a solution of carbon tetrachloride (40 mL) of (3-phenoxy-phenyl)-methanol (2.0 g) was added triphenylphosphine (3.2 g) at room temperature, which was heated to reflux under a nitrogen atmosphere for 5 hours and 40 minutes. The reaction mixture was cooled to room temperature and the solvent was evaporated under a reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=10:1) to obtain the titled compound (2.1 g).

Workup

  1. temperaturewhich was heated
  2. temperatureto reflux under a nitrogen atmosphere for 5 hours and 40 minutes
  3. customthe solvent was evaporated under a reduced pressure
  4. customThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-cd12e0ec162547c8ad4df9411c67a2ef
Source dataset
uspto-grants-2012_05
Patent number
US08183264B2

Reaction notes

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