Thionyl Chloride → 9-(Chloromethyl)anthracene

HRID 1956106Notes

Reaction equation

HRID 1956106 reaction equation
[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[CH2:15]O)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:19])=O>C(Cl)Cl.C1C=CC=CC=1>[Cl:19][CH2:15][C:13]1[C:14]2[C:5]([CH:6]=[C:7]3[C:12]=1[CH:11]=[CH:10][CH:9]=[CH:8]3)=[CH:4][CH:3]=[CH:2][CH:1]=2

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 738489-Anthracenemethanol

Product 1

HCID 323859-(Chloromethyl)anthraceneYield 94.1%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 9-anthracenemethanol (50 g, 0.24 mole) in methylene chloride (50 ml), a solution of thionyl chloride (32.3 g, 0.27 mole) in benzene (300 ml) was added, and reacted with stirring for 10 hours under reflux. The reaction mixture was poured into ice-water (500 ml). An organic layer separated was washed with H2O (100 ml×3), dried over anhydrous MgSO4 and evaporated to give 51.2 g of 9-chloromethylanthracene as residual crude orange yellow oil.

Workup

  1. customreacted
  2. temperatureunder reflux
  3. customAn organic layer separated
  4. washwas washed with H2O (100 ml×3)
  5. dry with materialdried over anhydrous MgSO4
  6. customevaporated

Sources & evidence

ORD record
ord-2e5b36182f694956845e6749e2e9aa41
Source dataset
uspto-grants-1998_07
Patent number
US05780206

Reaction notes

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