Acetyl chloride → 6-Methoxy-2-naphthylacetic acid

HRID 1076877

Reaction equation

HRID 1076877 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1.[C:13](Cl)(=[O:15])[CH3:14].[N+](C1C=CC=CC=1)([O-])=[O:18].[Cl-].[Al+3].[Cl-].[Cl-]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH2:14][C:13]([OH:15])=[O:18])[CH:7]=[CH:6]2

Participants

5

Reactant 4

HCID 6367Acetyl chlorideHCID 71192-MethoxynaphthaleneHCID 7416NitrobenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 321766-Methoxy-2-naphthylacetic acid

Conditions

Temperature
25 °C

Procedure

To a mixture of 1.6 g. of 2-methoxynaphthalene, 1.6 g. of acetyl chloride, and 20 ml. of nitrobenzene, there are added 4.0 g. of aluminum chloride. The resulting mixture is stirred for 48 hours at 25°C; then it is washed with water until free of chloride ion. The mixture is dried over sodium sulfate and evaporated under reduced pressure. The residue, 2-acetyl-6-methoxynaphthalene, is refluxed in 2 ml. of morpholine containing one-half gram of sulfur for 2 hours; the reaction mixture is then filtered and evaporated. The resulting reaction derivative is extracted with diethyl ether; the extracts are combined and evaporated. The residue is refluxed in 10 ml. of concentrated hydrochloric acid for 2 hours, cooled to 25°C, and neutralized with aqueous sodium hydroxide. The mixture is then extracted with ether and the extracts are combined, washed with water to neutrality, dried and evaporated to yield 2-(6-methoxy-2-naphthyl)acetic acid.

Workup

  1. additionTo a mixture of 1.6 g
  2. washthen it is washed with water until free of chloride ion
  3. dry with materialThe mixture is dried over sodium sulfate
  4. customevaporated under reduced pressure
  5. temperatureThe residue, 2-acetyl-6-methoxynaphthalene, is refluxed in 2 ml
  6. waitof morpholine containing one-half gram of sulfur for 2 hours
  7. filtrationthe reaction mixture is then filtered
  8. customevaporated
  9. customThe resulting reaction derivative
  10. extractionis extracted with diethyl ether
  11. customevaporated
  12. temperatureThe residue is refluxed in 10 ml
  13. waitof concentrated hydrochloric acid for 2 hours
  14. temperaturecooled to 25°C
  15. extractionThe mixture is then extracted with ether
  16. washwashed with water to neutrality
  17. customdried
  18. customevaporated

Sources & evidence

ORD record
ord-8ab6c9ad44534e0caa24da9165e57b33
Source dataset
uspto-grants-1976_05
Patent number
US03958012

Linked notes

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