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

HRID 1927261Notes

Reaction equation

HRID 1927261 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14]O)=[CH:10][CH:9]=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:11]1[CH:12]=[CH:13][C:8]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:9][CH:10]=1

Participants

4

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 826195(4-Phenoxyphenyl)methanol

Product 1

HCID 5209941-(Chloromethyl)-4-phenoxybenzene

Procedure

To a solution of carbon tetrachloride (8.2 mL) of (4-phenoxy-phenyl)-methanol (410 mg) was added triphenylphosphine (640 mg) at room temperature, which was heated to reflux for 7 hours and 40 minutes under a nitrogen atmosphere. 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 (410 mg).

Workup

  1. temperaturewhich was heated
  2. temperatureto reflux for 7 hours and 40 minutes under a nitrogen atmosphere
  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-141a01222a8e4fc6b86605776f323e98
Source dataset
uspto-grants-2012_05
Patent number
US08183264B2

Reaction notes

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