Oxalyl chloride → 4-Hexadecyloxyphenoxyacetic chloride

HRID 247995Notes

Reaction equation

HRID 247995 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-b08f9e8a478c4854963103cfebc3baab
Source dataset
uspto-grants-1993_05
Patent number
US05208247

Reaction notes

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