Benzenesulfinic acid, sodium salt → 6-hydroxy-5-[(phenylsulfonyl)methyl]-3,4-dihydro-1(2H)-naphthalenone

HRID 496435Notes

Reaction equation

HRID 496435 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].[C:15]1([S:21]([O-:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Na+]>C(#N)C>[OH:13][C:12]1[C:3]([CH2:2][S:21]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:23])=[O:22])=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:14])[CH2:7][CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 2723840Benzenesulfinic acid, sodium saltHCID 123936195-(chloromethyl)-6-hydroxy-3,4-dihydro-1(2H)-naphthalenone

Product 1

HCID 223247586-hydroxy-5-[(phenylsulfonyl)methyl]-3,4-dihydro-1(2H)-naphthalenoneYield 84%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 5-(chloromethyl)-6-hydroxy-3,4-dihydro-1(2H)-naphthalenone (10.0 g, 48 mmol), sodium phenylsulfinate (23.4 g, 142 mmol) and acetonitrile (100 mL) was stirred at reflux under nitrogen overnight. The mixture was poured onto ice. The precipitate was isolated by filtration, air dried, and crystallized from methanol-dichloromethane-ethyl acetate to give 6-hydroxy-5-[(phenylsulfonyl)methyl]-3,4-dihydro-1(2H)-naphthalenone as a cream solid, 12.16 g, 84% yield. NMR spectrum was consistent with structure.

Workup

  1. temperatureat reflux under nitrogen overnight
  2. additionThe mixture was poured onto ice
  3. customThe precipitate was isolated by filtration, air
  4. customdried
  5. customcrystallized from methanol-dichloromethane-ethyl acetate

Sources & evidence

ORD record
ord-7365dd8ecfbf4500937af44c7814b2c1
Source dataset
uspto-grants-2005_09
Patent number
US06943183B2

Reaction notes

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