Dimethylformamide → 2-(2,4-Di-t-butyl phenoxy)propionyl chloride

HRID 1488906Notes

Reaction equation

HRID 1488906 reaction equation
[C:1]([C:5]1[CH:16]=[C:15]([C:17]([CH3:20])([CH3:19])[CH3:18])[CH:14]=[CH:13][C:6]=1[O:7][CH:8]([CH3:12])[C:9](O)=[O:10])([CH3:4])([CH3:3])[CH3:2].CN(C=O)C.C(Cl)(=O)C([Cl:29])=O>C(Cl)Cl>[C:1]([C:5]1[CH:16]=[C:15]([C:17]([CH3:20])([CH3:19])[CH3:18])[CH:14]=[CH:13][C:6]=1[O:7][CH:8]([CH3:12])[C:9]([Cl:29])=[O:10])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 167740552-(2,4-Di-t-butyl phenoxy) propionic acid

Product 1

HCID 136513232-(2,4-Di-t-butyl phenoxy)propionyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred slurry of 2-(2,4-di-t-butyl phenoxy) propionic acid (27.8 g, 0.100 mol) in CH2Cl2 (280 mL) with 2 mL of DMF, oxalyl chloride (17.0 g, 0.134 mol) was added dropwise. The solution resulted after several minutes was stirred for 2 hr. TLC indicates no starting material. The solution was filtered through a glass wool plug to remove some debris and the filtrate was concentrated in vacuo, residue was washed with CH2Cl2 (50 mL) and was concentrated once more to give a gelatinous mixture, which was used without further purification.

Workup

  1. customThe solution resulted after several minutes
  2. filtrationThe solution was filtered through a glass wool plug
  3. customto remove some debris
  4. concentrationthe filtrate was concentrated in vacuo, residue
  5. washwas washed with CH2Cl2 (50 mL)
  6. concentrationwas concentrated once more
  7. customto give a gelatinous mixture, which
  8. customwas used without further purification

Sources & evidence

ORD record
ord-a5cc76837bdc4e1ba6d08b6165e5aa40
Source dataset
uspto-grants-1997_10
Patent number
US05677118

Reaction notes

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