Methanol → 2-Chloro-6-chloromethylnaphthalene

HRID 973296Notes

Reaction equation

HRID 973296 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH:12]=[C:11]([CH2:16]O)[CH:10]=[CH:9]2.CO>N1C=CC=CC=1.C(Cl)(Cl)Cl>[Cl:3][CH2:16][C:11]1[CH:10]=[CH:9][C:8]2[C:13](=[CH:14][CH:15]=[C:6]([Cl:5])[CH:7]=2)[CH:12]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 13384253(6-Chloronaphthalen-2-yl)methanol

Product 1

HCID 133842552-Chloro-6-chloromethylnaphthaleneYield 95.7%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent

Conditions

Temperature
20 °C

Procedure

Thionyl chloride (99.4 g.) is added dropwise at 0° C. during 1 hour to a stirred suspension of the 6-chloro-2-hydroxymethylnaphthalene (96.3 g.) in a mixture of pyridine (59.0 g.) and chloroform (2 3 l). The mixture is stirred for 1 hour at 20° C., then treated dropwise with methanol (60 ml.) and stored for 18 hours. The solution is washed with water, 3N-hydrochloric acid, and water again, dried with magnesium sulphate and evaporated. The residue is crystallised from light petroleum (b.p. 80°-100° C.) to give 2-chloromethyl-6-chloronaphthalene (101 g.) m.p. 107°-110° C. raised to 110°-111° C. by further crystallisation.

Workup

  1. waitstored for 18 hours
  2. washThe solution is washed with water, 3N-hydrochloric acid, and water again
  3. dry with materialdried with magnesium sulphate
  4. customevaporated
  5. customThe residue is crystallised from light petroleum (b.p. 80°-100° C.)

Sources & evidence

ORD record
ord-b2bad1cb85994e0889e1bf6222282bd6
Source dataset
uspto-grants-1977_10
Patent number
US04055595

Reaction notes

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