1-Naphthaleneacetic Acid → 1-Acenaphthenone

HRID 2230264Notes

Reaction equation

HRID 2230264 reaction equation
C(Cl)(=O)C(Cl)=O.[C:7]1([CH2:17][C:18]([OH:20])=O)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl.CN(C)C=O>[C:18]1(=[O:20])[C:15]2=[C:16]3[C:11](=[CH:12][CH:13]=[CH:14]2)[CH:10]=[CH:9][CH:8]=[C:7]3[CH2:17]1

Participants

6

Reactant 3

HCID 68621-Naphthaleneacetic AcidHCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 752291-Acenaphthenone

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

In a 1 litre three-necked flask, oxalyl chloride (2.87 ml, 3.22.10−2 mol, 1 eq.) is added dropwise, under argon, to a solution of (naphth-1-yl)acetic acid (6 g, 3.22.10−2 mol) in anhydrous dichloromethane (270 ml) at 0° C. A few drops of anhydrous dimethylformamide are then added. After 1 hour at 0° C., slight evolution of gas is still observed and the three-necked flask is left at ambient temperature for 40 minutes. After return to 0° C., aluminium chloride (11.2 g, 8.38.10−2 mol, 2.6 eq.) is added gradually with a spatula. The solution is stirred for twenty minutes and becomes green-black in colour. The mixture is poured into an ice/1N HCl mixture. After separation of the phases and washings of the acidic aqueous phase with dichloromethane, the combined organic phases are washed with water, then treated with a saturated NaHCO3 solution and finally washed with a saturated NaCl solution. After drying over MgSO4 and evaporation under reduced pressure, the title product is obtained in the form of a yellow solid.

Workup

  1. waitthe three-necked flask is left at ambient temperature for 40 minutes
  2. customAfter separation of the phases and washings of the acidic aqueous phase with dichloromethane
  3. washthe combined organic phases are washed with water
  4. additiontreated with a saturated NaHCO3 solution
  5. washfinally washed with a saturated NaCl solution
  6. dry with materialAfter drying over MgSO4 and evaporation under reduced pressure

Sources & evidence

ORD record
ord-1cc7eb118e0744cbae83abef0c20663a
Source dataset
uspto-grants-2002_07
Patent number
US06423870B1

Reaction notes

Loading…