Dimethylformamide → 3-(Tetradecyloxy)benzoyl chloride

HRID 247936Notes

Reaction equation

HRID 247936 reaction equation
[CH2:1]([O:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=1)[C:19](O)=[O:20])[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].CN(C)C=O.C(Cl)(=O)C([Cl:33])=O>C(Cl)Cl>[CH2:1]([O:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=1)[C:19]([Cl:33])=[O:20])[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 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 32623113-(Tetradecyloxy)benzoic acid

Product 1

HCID 190149493-(Tetradecyloxy)benzoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 5.0 g of product from Example 23, 0.055 g of dimethylformamide and 70 ml of methylene chloride is added 1.96 ml of oxalyl chloride. The reaction is stirred at room temperature for 22 hours and concentrated. The residue is dissolved in diethyl ether, filtered and concentrated to give 5.28 g of the desired product as cream crystals.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue is dissolved in diethyl ether
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d5ae8f63fb2d41969ca56e994ac5fbd1
Source dataset
uspto-grants-1993_05
Patent number
US05208247

Reaction notes

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