Oxalyl chloride → HCID 10090356, compound

HRID 484583Notes

Reaction equation

HRID 484583 reaction equation
[CH2:1]([O:15][C:16]1[CH:17]=[C:18]([CH2:22][C:23]([OH:25])=O)[CH:19]=[CH:20][CH:21]=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>C(Cl)Cl.CN(C)C=O>[CH2:1]([O:15][C:16]1[CH:17]=[C:18]([CH2:22][C:23]([Cl:29])=[O:25])[CH:19]=[CH:20][CH:21]=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 10315754HCID 10315754, compound

Product 1

HCID 10090356HCID 10090356, compoundYield 101.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 20 g of m-tetradecyloxyphenylacetic acid, 10.93 g of oxalyl chloride and 41.95 mg of N,N-dimethylformamide in 250 ml of methylene chloride is stirred at ambient temperature for 5 hours. The solvent is removed and the concentrate dissolved in 1:1 ether:hexane and filtered through diatomaceous earth. The filtrate is evaporated to give 21.3 g of the desired product as a light yellow solid.

Workup

  1. customThe solvent is removed
  2. dissolutionthe concentrate dissolved in 1:1 ether
  3. filtrationhexane and filtered through diatomaceous earth
  4. customThe filtrate is evaporated

Sources & evidence

ORD record
ord-4ce4cee03469498b830761e30a2aa0a8
Source dataset
uspto-grants-1993_07
Patent number
US05231182

Reaction notes

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