Oxalyl chloride → 4-Hexadecyloxyphenoxyacetic chloride

HRID 1728865Notes

Reaction equation

HRID 1728865 reaction equation
[CH2:1]([O:17][C:18]1[CH:28]=[CH:27][C:21]([O:22][CH2:23][C:24](O)=[O:25])=[CH:20][CH:19]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C(Cl)(=O)C([Cl:32])=O>CN(C)C=O.C(Cl)Cl>[CH2:1]([O:17][C:18]1[CH:28]=[CH:27][C:21]([O:22][CH2:23][C:24]([Cl:32])=[O:25])=[CH:20][CH:19]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 9977851[4-(Hexadecyloxy)phenoxy]acetic acid

Product 1

HCID 104317244-Hexadecyloxyphenoxyacetic chlorideYield 97.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 13.2 g of product from Example 86, 6.4 g of oxalyl chloride, 225 ml of methylene chloride and 5 drops of dimethylformamide is stirred at room temperature for 17 hours. The solvent is concentrated in vacuo, the residue is dissolved in ether, filtered through diatomaceous earth and concentrated in vacuo to give 13.5 g of the desired product.

Workup

  1. concentrationThe solvent is concentrated in vacuo
  2. dissolutionthe residue is dissolved in ether
  3. filtrationfiltered through diatomaceous earth
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f0a56ed431dc45a797ab682877c51f32
Source dataset
uspto-grants-1994_07
Patent number
US05328921

Reaction notes

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