Triethylamine → 2-(Chloromethyl)-1-methylnaphthalene

HRID 1719565Notes

Reaction equation

HRID 1719565 reaction equation
O[CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[CH3:13].C(N(CC)CC)C.CS([Cl:25])(=O)=O>C(Cl)Cl>[Cl:25][CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[CH3:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 15054223HCID 15054223, compound

Product 1

HCID 199951842-(Chloromethyl)-1-methylnaphthalene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 10.1 g of 2-hydroxymethyl-1-methylnaphthalene, 14.0 ml of triethylamine and 120 ml of methylene dichloride, cooled in an ice-salt bath was added dropwise 5.5 ml of methanesulfonyl chloride. The reaction mixture was allowed to warm to room temperature, washed with water, dried and concentrated in vacuo to obtain 8.4 g of 2-chloromethyl-1-methylnaphthalene as a waxy solid.

Workup

  1. temperaturecooled in an ice-salt bath
  2. washwashed with water
  3. customdried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-278beff3604d465fbd23d39ecb01fa59
Source dataset
uspto-grants-1985_09
Patent number
US04540705

Reaction notes

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