Oxalyl chloride → p-Tetradecyloxyphenylacetylchloride

HRID 653761Notes

Reaction equation

HRID 653761 reaction equation
[CH2:1]([O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]([OH:25])=O)=[CH:18][CH:17]=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][CH3:14].C(Cl)(=O)C([Cl:29])=O>CN(C)C=O.C(Cl)Cl>[CH2:1]([O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]([Cl:29])=[O:25])=[CH:18][CH:17]=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][CH3:14]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 10472964p-Tetradecyloxyphenylacetic acid

Product 1

HCID 10021844p-TetradecyloxyphenylacetylchlorideYield 97.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 21.7 g of p-tetradecyloxyphenylacetic acid and 11.85 g of oxalyl chloride, 45.5 mg of N,N-dimethylformamide and 250 ml of methylene chloride is stirred at ambient temperature for 24 hours. The solvent is removed by evaporation and the residue is dissolved in ether and filtered through diatomaceous earth. The filtrate is evaporated to give 22.3 g of the desired product as a white solid.

Workup

  1. customThe solvent is removed by evaporation
  2. dissolutionthe residue is dissolved in ether
  3. filtrationfiltered through diatomaceous earth
  4. customThe filtrate is evaporated

Sources & evidence

ORD record
ord-9644c299747e45b0a243384c5b3a6d9a
Source dataset
uspto-grants-1992_07
Patent number
US05128351

Reaction notes

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