Oxalyl chloride → HCID 21710470, compound

HRID 2192464Notes

Reaction equation

HRID 2192464 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH:12]([CH3:14])[CH3:13])[C:5](O)=[O:6].C(Cl)(=O)C([Cl:18])=O>CN(C=O)C.ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH:12]([CH3:14])[CH3:13])[C:5]([Cl:18])=[O:6]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 225977283-Chloro-4-(propan-2-yloxy)benzoic acid

Product 1

HCID 21710470HCID 21710470, compoundYield 96.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

3-Chloro-4-[(1-methylethyl)oxy]benzoic acid (D3; 4 g, 18. mmol), dichloromethane (DCM) (30 ml), oxalyl chloride (1.88 ml, 21.4 mmol) and DMF (1.4 μl, 0.019 mmol) were stirred under a blanket of nitrogen for 18 h. The solvent was removed in vacuo to give a yellow oil which crystallised on standing. The solid was dissolved in DCM and the solvent was removed in vacuo to give the title compound as a yellow solid (4.2 g).

Workup

  1. customThe solvent was removed in vacuo
  2. customto give a yellow oil which
  3. customcrystallised
  4. dissolutionThe solid was dissolved in DCM
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-175c50e60fd844a0903dd5963291c8e1
Source dataset
uspto-grants-2012_12
Patent number
US08329730B2

Reaction notes

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