Thionyl Chloride → 2-(Chloromethyl)naphthalene

HRID 352343

Reaction equation

HRID 352343 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11]O.S(Cl)([Cl:15])=O>C1(C)C=CC=CC=1.ClCCl>[Cl:15][CH2:11][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 741282-Naphthalenemethanol

Product 1

HCID 756322-(Chloromethyl)naphthalene

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To 1.26 mol of naphth-2-yl-methanol in 1.5 liters of toluene there are slowly added 3.8 mol of thionyl chloride. The mixture is then heated at reflux for two hours. After cooling, the solvent is evaporated off. The crude product is taken up in toluene twice and evaporated. The oil obtained is taken up in dichloromethane, washed and dried. After filtering and evaporating, the oil obtained is distilled to yield the expected product.

Workup

  1. temperatureThe mixture is then heated
  2. temperatureat reflux for two hours
  3. temperatureAfter cooling
  4. customthe solvent is evaporated off
  5. customevaporated
  6. customThe oil obtained
  7. washwashed
  8. customdried
  9. filtrationAfter filtering
  10. customevaporating
  11. customthe oil obtained
  12. distillationis distilled

Sources & evidence

ORD record
ord-2b76a36fe9d8421e9983fe191e681c45
Source dataset
uspto-grants-2004_06
Patent number
US06747032B2

Linked notes

Loading…