Dimethylformamide → 3-(Tetradecyloxy)benzoyl chloride

HRID 1728811Notes

Reaction equation

HRID 1728811 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 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-f3573b2a1e8f489c8eb1b7eafdc3efb4
Source dataset
uspto-grants-1994_07
Patent number
US05328921

Reaction notes

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