Dimethylformamide → 3-Methoxy-4-(tetradecyloxy)benzeneacetyl chloride

HRID 247977Notes

Reaction equation

HRID 247977 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:24][C:25]([OH:27])=O)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].CN(C)C=O.C(Cl)(=O)C([Cl:36])=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:24][C:25]([Cl:36])=[O:27])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 190147993-Methoxy-4-(tetradecyloxy)benzeneacetic acid

Product 1

HCID 190150653-Methoxy-4-(tetradecyloxy)benzeneacetyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 10 g of product from Example 67, 0.0965 g of dimethylformamide and 150 ml of methylene chloride is added dropwise 3.46 ml of oxalyl chloride. The reaction is stirred at room temperature for 20 hours and the solvent concentrated in vacuo. The residue is dissolved in diethyl ether, filtered and concentrated in vacuo to give 10.5 g of the desired product as colorless needles.

Workup

  1. concentrationthe solvent concentrated in vacuo
  2. dissolutionThe residue is dissolved in diethyl ether
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f8595e1e00a5412f92a9f87513fe062d
Source dataset
uspto-grants-1993_05
Patent number
US05208247

Reaction notes

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