Naphthalene → 2-(4-Chlorobutyryl)naphthalene

HRID 1758290Notes

Reaction equation

HRID 1758290 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][CH2:6][CH2:7][CH2:8][C:9](Cl)=[O:10].[CH:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1>[N+](C1C=CC=CC=1)([O-])=O>[Cl:5][CH2:6][CH2:7][CH2:8][C:9]([C:14]1[CH:13]=[CH:12][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=1)=[O:10]

Participants

5

Reactant 3

HCID 931NaphthaleneHCID 783704-Chlorobutyryl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 122875592-(4-Chlorobutyryl)naphthaleneYield 18.1%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Procedure

Aluminum chloride (26.7 g) is added to nitrobenzene (20 ml) and 4-chlorobutyric acid chloride (15.5 g) is added dropwise to the mixture with ice-cooling. Naphthalene (12.8 g) is slowly added to the mixture with ice-cooling and stirring is continued at the same temperature for 30 minutes. After stirring at room temperature for additional 2 hours, the reaction mixture is poured into ice-hydrochloric acid and extracted with chloroform. The chloroform extract is washed with water, saturated aqueous sodium bicarbonate, water and then saturated aqueous sodium chloride and dried over anhydrous sodium sulfate. The dried solution is distilled. A fraction having b.p. 187°-191° C./1.6 mmHg is separated and purified by silica gel column chromatography. The product thus obtained is crystallized from hexane and then further recrystallized from hexane-petroleum ether to obtain 2-(4-chlorobutyryl)naphthalene (4.2 g) as colorless flakes, m.p. 43°-44° C.

Workup

  1. additionis added dropwise to the mixture with ice-
  2. temperaturecooling
  3. temperaturecooling
  4. stirringAfter stirring at room temperature for additional 2 hours
  5. extractionextracted with chloroform
  6. extractionThe chloroform extract
  7. washis washed with water, saturated aqueous sodium bicarbonate, water
  8. dry with materialsaturated aqueous sodium chloride and dried over anhydrous sodium sulfate
  9. distillationThe dried solution is distilled
  10. customis separated
  11. custompurified by silica gel column chromatography
  12. customThe product thus obtained
  13. customis crystallized from hexane
  14. customfurther recrystallized from hexane-petroleum ether

Sources & evidence

ORD record
ord-28476733a80d43e1af88f3ceefc4becb
Source dataset
uspto-grants-1983_02
Patent number
US04372953

Reaction notes

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