Thionyl Chloride → 6-(Chlorocarbonyl)naphthalen-2-yl acetate

HRID 333568Notes

Reaction equation

HRID 333568 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[C:10]([C:15]([OH:17])=O)[CH:9]=[CH:8]2)(=[O:3])[CH3:2].S(Cl)([Cl:20])=O>CN(C)C=O.C1COCC1>[C:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[C:10]([C:15]([Cl:20])=[O:17])[CH:9]=[CH:8]2)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 870386-(Acetyloxy)-2-naphthalenecarboxylic acid

Product 1

HCID 157248096-(Chlorocarbonyl)naphthalen-2-yl acetate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Into a 0.25 L, 3-necked roundbottom flask, fitted with a magnetic stirbar, addition funnel, and reflux condenser were added 6-acetoxy-2-naphthoic acid (30.0 g, 130 mmol), THF (135 mL) and dimethylformamide (approx. 20 drops). Thionyl chloride (18.6 g, 156 mmol) was added slowly dropwise to the reaction mixture over 15 minutes. The reaction mixture was heated to reflux for 2.5 hours under nitrogen and allowed to cool to room temperature overnight.

Workup

  1. customInto a 0.25 L, 3-necked roundbottom flask, fitted with a magnetic stirbar, addition funnel
  2. temperaturereflux condenser
  3. temperatureThe reaction mixture was heated
  4. temperatureto reflux for 2.5 hours under nitrogen

Sources & evidence

ORD record
ord-518c529df37c48548f940ae26606df2d
Source dataset
uspto-grants-2014_11
Patent number
US08883407B2

Reaction notes

Loading…