1-Naphthaleneacetic Acid → 1-Acenaphthenone

HRID 1675369Notes

Reaction equation

HRID 1675369 reaction equation
[C:1]1([CH2:11][C:12]([OH:14])=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.S(Cl)(Cl)=O.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[C:12]1(=[O:14])[C:9]2=[C:10]3[C:5](=[CH:6][CH:7]=[CH:8]2)[CH:4]=[CH:3][CH:2]=[C:1]3[CH2:11]1

Participants

5

Reactant 3

HCID 68621-Naphthaleneacetic AcidHCID 24386Thionyl ChlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 752291-AcenaphthenoneYield 89.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Naphthylacetic acid (100 g, 530 mmol) was dissolved in dichloromethane (15 ml). Thionyl chloride (158 g, 1.32 mol) was added under ice-cooling and the mixture was heated under reflux for 1 hr. The solvent was evaporated and 1,2-dichloroethane (500 ml) was added to the obtained residue for dissolution. Aluminum chloride (150 g, 1.12 mol) was added under ice-cooling, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into ice water, and the mixture was extracted with dichloromethane. The extract was washed with water and saturated brine, dried over magnesium sulfate and concentrated to give acenaphthen-1-one (80 g) as yellow crystals.

Workup

  1. temperaturecooling
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 1 hr
  4. customThe solvent was evaporated
  5. addition1,2-dichloroethane (500 ml) was added to the obtained residue for dissolution
  6. temperaturecooling
  7. extractionthe mixture was extracted with dichloromethane
  8. washThe extract was washed with water and saturated brine
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-4f3f2934079043e694cdfd7466e4f163
Source dataset
uspto-grants-2011_08
Patent number
US08003669B2

Reaction notes

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