Sodium methanesulfinate → 5-methanesulfonylmethyl-6-hydroxy-3,4-dihydro-1(2H)-naphthalenone

HRID 259009Notes

Reaction equation

HRID 259009 reaction equation
Cl[CH2:2][C:3]1[C:12]([OH:13])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][C:8]2=[O:14].[CH3:15][S:16]([O-:18])=[O:17].[Na+]>C(O)C>[CH3:15][S:16]([CH2:2][C:3]1[C:12]([OH:13])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][C:8]2=[O:14])(=[O:18])=[O:17]

Participants

4

Reactant 2

HCID 2733271Sodium methanesulfinateHCID 123936195-(chloromethyl)-6-hydroxy-3,4-dihydro-1(2H)-naphthalenone

Product 1

HCID 132865845-methanesulfonylmethyl-6-hydroxy-3,4-dihydro-1(2H)-naphthalenone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 100 ml. of ethanol are added 10 g. of 5-chloromethyl-6-hydroxy-3,4-dihydro-1(2H)-naphthalenone and 5.4 g. of sodium methanesulfinate, and the mixture is heated on reflux for 2 hours. Then, the reaction mixture is concentrated and the residue is dissolved in chloroform and washed with water. The chloroform layer is dried in the conventional manner and the chloroform is distilled off. The procedure provides 5-methanesulfonylmethyl-6-hydroxy-3,4-dihydro-1(2H)-naphthalenone melting at 225° -230° C(decomp.).

Workup

  1. temperatureon reflux for 2 hours
  2. concentrationThen, the reaction mixture is concentrated
  3. dissolutionthe residue is dissolved in chloroform
  4. washwashed with water
  5. dry with materialThe chloroform layer is dried in the conventional manner
  6. distillationthe chloroform is distilled off

Sources & evidence

ORD record
ord-18d17fd6f9784ef5a59d3cfd35256d89
Source dataset
uspto-grants-1977_07
Patent number
US04035512

Reaction notes

Loading…