Oxalyl chloride → HCID 18466196, compound

HRID 2230261Notes

Reaction equation

HRID 2230261 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]=1[CH2:19][CH2:20][C:21]([OH:23])=O.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl.CN(C)C=O>[CH3:7][O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11]3[C:10]=1[CH2:19][CH2:20][C:21](=[O:23])[C:12]=3[CH:13]=[CH:14][CH:15]=2

Participants

6

Reactant 3

HCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 91498873-(2-methoxynaphthalen-1-yl)propanoic Acid

Product 1

HCID 18466196HCID 18466196, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

In a 250 ml three-necked flask, oxalyl chloride (1.95 ml, 2.19.10−2 mol, 1 eq.) is added dropwise, under argon, to a solution of the acid obtained in Step D (5 g, 2.17.10−2 mol) in anhydrous dichloromethane (225 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 (7.5 g, 5.62.10−2 mol, 2.6 eq.) is added using a spatula. The initially yellow solution becomes red, orange and then khaki-green. After 15 minutes' stirring at 0° C., 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 yellow oil obtained crystallises in a freezer.

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
  7. customthe yellow oil obtained
  8. customcrystallises in a freezer

Sources & evidence

ORD record
ord-7f5dbef607d1483494a65227234eef45
Source dataset
uspto-grants-2002_07
Patent number
US06423870B1

Reaction notes

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