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

HRID 77870Notes

Reaction equation

HRID 77870 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-benzeneYield 86%

Procedure

A mixture of (4-butoxymethyl-phenyl)-methanol (190 mg, 0.98 mmol) described in Manufacturing Example 33-1-3, triphenylphosphine (310 mg, 1.2 mmol) and carbon tetrachloride (3 mL) was stirred under reflux for 7 hours. The reaction mixture was cooled to room temperature, and concentrated under a reduced pressure. The residue was purified by neutral silica gel column chromatography (ethyl acetate:heptane=1:15) to obtain the title compound (180 mg, 86%).

Workup

  1. temperatureunder reflux for 7 hours
  2. concentrationconcentrated under a reduced pressure
  3. customThe residue was purified by neutral silica gel column chromatography (ethyl acetate:heptane=1:15)

Sources & evidence

ORD record
ord-851bb41524274c81898e186bee7adc52
Source dataset
uspto-grants-2014_09
Patent number
US08841327B2

Reaction notes

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