Thionyl Chloride → 1-(Chloromethyl)-4-(dodecyloxy)benzene

HRID 1440658Notes

Reaction equation

HRID 1440658 reaction equation
[CH2:1]([O:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]O)=[CH:16][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].S(Cl)([Cl:24])=O>C1C=CC=CC=1>[CH2:1]([O:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][Cl:24])=[CH:16][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 144776284-Dodecyloxybenzyl alcohol

Product 1

HCID 100867551-(Chloromethyl)-4-(dodecyloxy)benzene

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 4-dodecyloxybenzyl alcohol (Preparation 1, 2.92 g, 0.0010 M) in benzene (40 mL) is added dropwise to a stirred solution of thionyl chloride (3.0 mL, 4.97 g, 0.04 M) over a period of 20 minutes. The solution is stirred at room temperature for 0.5 hr and then is heated at reflux temperature for 3 hours (monitoring of the reaction by TLC may be deceptive since the product is hydrolyzed to starting alcohol when placed on a silica gel plate; the plate must be developed immediately after the sample is applied). Benzene and excess thionyl chloride are removed under reduced pressure. The crude product is used in Example 1 without further purification.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 3 hours (
  3. custommonitoring of the reaction by TLC
  4. customBenzene and excess thionyl chloride are removed under reduced pressure
  5. customThe crude product is used in Example 1 without further purification

Sources & evidence

ORD record
ord-036afde07b0a4a5cbb947b04027f5248
Source dataset
uspto-grants-1996_03
Patent number
US05500417

Reaction notes

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