Thionyl Chloride → HCID 20541717, compound

HRID 1863474Notes

Reaction equation

HRID 1863474 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([CH3:15])[C:12]=1[O:13][CH3:14])[CH:9]=[C:8]([CH2:16][C:17]([OH:19])=O)[CH:7]=[CH:6]2.S(Cl)([Cl:22])=O>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([CH3:15])[C:12]=1[O:13][CH3:14])[CH:9]=[C:8]([CH2:16][C:17]([Cl:22])=[O:19])[CH:7]=[CH:6]2

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 12849308HCID 12849308, compound

Product 1

HCID 20541717HCID 20541717, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 24.0 g. of 6,7-dimethoxy-8-methyl-2-naphthaleneacetic acid and 30 ml. of thionyl chloride in 250 ml. of benzene was kept at 40° C. one hour and then overnight at room temperature. The reaction mixture was then evaporated to dryness in vacuo at 50° C. Additional benzene was added and evaporation repeated to give 6,7-dimethoxy-8-methyl-2-naphthaleneacetyl chloride. An infrared spectrum indicated no remaining carboxylic acid and this material was used directly in the preparation of 6,7-dimethoxy-8-methyl-2-naphthaleneacetamide as described hereinabove in Example 98.

Workup

  1. additionA mixture of 24.0 g
  2. customovernight
  3. customat room temperature
  4. customThe reaction mixture was then evaporated to dryness in vacuo at 50° C
  5. additionAdditional benzene was added
  6. customevaporation

Sources & evidence

ORD record
ord-bf5aea95327341cea2f3bce0a1936466
Source dataset
uspto-grants-1979_09
Patent number
US04169108

Reaction notes

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