Thionyl Chloride → 6,7-Dimethoxy-2-naphthoyl chloride

HRID 1863475Notes

Reaction equation

HRID 1863475 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9]=[C:8]([C:15]([OH:17])=O)[CH:7]=[CH:6]2.S(Cl)([Cl:20])=O>CN(C)C=O.C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9]=[C:8]([C:15]([Cl:20])=[O:17])[CH:7]=[CH:6]2

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 2830286,7-Dimethoxy-2-naphthoic acid

Product 1

HCID 218249396,7-Dimethoxy-2-naphthoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 241BenzeneSolvent

Procedure

To a solution containing 15.0 g. of 6,7-dimethoxy-2-naphthoic acid and one drop of dimethylformamide in 200 ml. of benzene was added 25 ml. of thionyl chloride. After heating one hour under reflux the mixture was evaporated to dryness in vacuo. Additional benzene was added and evaporation repeated to give 6,7-dimethoxy-2-naphthoyl chloride which was used directly in the preparation of 6,7-dimethoxy-2-naphthamide as described hereinabove in Example 113.

Workup

  1. additionTo a solution containing 15.0 g
  2. temperatureAfter heating one hour
  3. temperatureunder reflux the mixture
  4. customwas evaporated to dryness in vacuo
  5. additionAdditional benzene was added
  6. customevaporation

Sources & evidence

ORD record
ord-4501dfb1c86a418b9cade2b8f6690a3d
Source dataset
uspto-grants-1979_09
Patent number
US04169108

Reaction notes

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