Hydrochloric Acid → HCID 12791517, compound

HRID 1389142Notes

Reaction equation

HRID 1389142 reaction equation
[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[C:14](Cl)(=[O:16])[CH3:15].[Cl-].[Al+3].[Cl-].[Cl-].Cl>[N+](C1C=CC=CC=1)([O-])=O>[C:14]([C:4]1[CH:3]=[C:2]([F:1])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[CH:5]=1)(=[O:16])[CH3:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 111480321-fluoro-7-methoxynaphthalene

Product 1

HCID 12791517HCID 12791517, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Procedure

A solution of 1-fluoro-7-methoxynaphthalene (13 g, 0.074 mol) and acetyl chloride (8.01 g, 0.10 mol) in nitrobenzene (120 ml) was treated at 0° C. with powdered anhydrous aluminium chloride (15.59 g, 0.11 mol) over a period of 30 minutes. After stirring at room temperature overnight, the reaction mixture was treated with a mixture of ice (50 g) and concentrated hydrochloric acid (20 ml). The mixture was steam distilled until removal of nitrobenzene was complete. The residue was cooled and the product extracted into ether. The ether layers were washed, dried and concentrated to give a brown solid which was purified by column chromatography on silica gel using petroleum ether/ether mixture as eluant. The product was recrystallised from ether to give a coloured solid 5.33 g. m.p. 96°-7° C.

Workup

  1. distillationdistilled until removal of nitrobenzene
  2. temperatureThe residue was cooled
  3. extractionthe product extracted into ether
  4. washThe ether layers were washed
  5. customdried
  6. concentrationconcentrated
  7. customto give a brown solid which
  8. customwas purified by column chromatography on silica gel
  9. customThe product was recrystallised from ether

Sources & evidence

ORD record
ord-2af36e2fccb34efa92661c0f0ddfd359
Source dataset
uspto-grants-1981_01
Patent number
US04243682

Reaction notes

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