Oxalyl chloride → 4-Hexadecyloxyphenoxyacetic chloride

HRID 1461925Notes

Reaction equation

HRID 1461925 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 100.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 13.2 g of [4-(hexadecyloxy)phenoxy]acetic acid, 6.4 g of oxalyl chloride, 225 ml of methylene chloride and 5 drops of N,N-dimethylformamide is stirred at ambient temperature for 17 hours. The solvent is evaporated to a residue which is dissolved in ether and filtered through diatomaceous earth. The filtrate is evaporated to give 13.9 g of the desired product as a white solid.

Workup

  1. customThe solvent is evaporated to a residue which
  2. dissolutionis dissolved in ether
  3. filtrationfiltered through diatomaceous earth
  4. customThe filtrate is evaporated

Sources & evidence

ORD record
ord-cf5a458d9acf4365903d8f4f879c28b3
Source dataset
uspto-grants-1991_12
Patent number
US05077409

Reaction notes

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