Thionyl Chloride → Fluoranthene, 1-(chloromethyl)-

HRID 2255820Notes

Reaction equation

HRID 2255820 reaction equation
O[CH2:2][C:3]1[C:17]2=[C:18]3[C:10]([C:11]4[C:16]2=[CH:15][CH:14]=[CH:13][CH:12]=4)=[CH:9][CH:8]=[CH:7][C:6]3=[CH:5][CH:4]=1.O=S(Cl)[Cl:21]>C1(C)C=CC=CC=1>[Cl:21][CH2:2][C:3]1[C:17]2=[C:18]3[C:10]([C:11]4[C:16]2=[CH:15][CH:14]=[CH:13][CH:12]=4)=[CH:9][CH:8]=[CH:7][C:6]3=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 1544331-Hydroxymethylfluoranthene

Product 1

HCID 152291Fluoranthene, 1-(chloromethyl)-

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a RB flask equipped with magnetic stirring bar, condenser, addition funnel, thermometer and N2 inlet line with bubbler was added 1-hydroxymethylfluoranthene (3B, 12.0 g, 0.052 mol), and dry PhCH3 (500 mL). To the mixture was added SOCl2 (Aldrich, 15.73 g, 0.132 mol, 9.5 mL) dropwise over 15 min. The mixture was then heated at 80° overnight and then refluxed for 1 h. The solvent was removed by rotary evaporation to give a crude off white solid. The material was redissolved in PhCH3 (300 mL) followed again by rotary evaporation. The process was repeated two additional times to give the crude product 1-chloromethylfluoranthene which was used without further purification.

Workup

  1. customTo a RB flask equipped with magnetic stirring bar, condenser, addition funnel
  2. temperatureThe mixture was then heated at 80° overnight
  3. temperaturerefluxed for 1 h
  4. customThe solvent was removed by rotary evaporation
  5. customto give a crude off white solid
  6. customfollowed again by rotary evaporation

Sources & evidence

ORD record
ord-415362ab5d5546458b1bfed2bdfa1682
Source dataset
uspto-grants-1993_08
Patent number
US05241107

Reaction notes

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