Carbon Tetrachloride → 1-Butoxymethyl-4-chloromethyl-benzene

HRID 1927267Notes

Reaction equation

HRID 1927267 reaction equation
[CH2:1]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13]O)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH3:4].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:35]>>[CH2:1]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][Cl:35])=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 54087706(4-Butoxymethyl-phenyl)-methanol

Product 1

HCID 592551091-Butoxymethyl-4-chloromethyl-benzene

Procedure

A mixture of (4-butoxymethyl-phenyl)-methanol (190 mg) described in Manufacturing Example 43-3, triphenylphosphine (310 mg), and carbon tetrachloride (3 mL) was heated to reflux for 7 hours. The reaction mixture was cooled to room temperature, and then the solvent was evaporated under a reduced pressure. The residue was purified by neutral silica gel column chromatography (ethyl acetate:heptane=1:15) to obtain the titled compound (180 mg).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 7 hours
  3. customthe solvent was evaporated under a reduced pressure
  4. customThe residue was purified by neutral silica gel column chromatography (ethyl acetate:heptane=1:15)

Sources & evidence

ORD record
ord-963f0146572644f88a794fb0c53e26ff
Source dataset
uspto-grants-2012_05
Patent number
US08183264B2

Reaction notes

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