Thionyl Chloride → Benzene, (chloromethyl)phenoxy-

HRID 1613257Notes

Reaction equation

HRID 1613257 reaction equation
[O:1]([C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[CH2:10]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:18])=O>C1C=CC=CC=1>[O:1]([C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[CH2:10][Cl:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 36601112-Phenoxybenzyl alcohol

Product 1

HCID 169302Benzene, (chloromethyl)phenoxy-Yield 106.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Into a 1 liter round bottom flask equipped with a stirrer, a condenser, a thermometer and an addition funnel are charged 25 g (0.125 mole) of o-phenoxybenzyl alcohol and 250 ml of benzene. Thionyl chloride (18.0 g, 0.15 mole) is added dropwise at room temperature. After the addition, the reaction mixture is heated to reflux for 2 hours. Solvent is then evaporated under vacuum to give 29 g of product.

Workup

  1. customInto a 1 liter round bottom flask equipped with a stirrer, a condenser
  2. additionAfter the addition
  3. temperaturethe reaction mixture is heated
  4. temperatureto reflux for 2 hours
  5. customSolvent is then evaporated under vacuum

Sources & evidence

ORD record
ord-2e6b1368490945298faa6c94782a96b4
Source dataset
uspto-grants-1993_03
Patent number
US05192783

Reaction notes

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