Oxalyl chloride → 3-(1,1-Dimethylethyl)-4-(tetradecyloxy)benzoyl chloride

HRID 247942Notes

Reaction equation

HRID 247942 reaction equation
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:8](O)=[O:9])([CH3:4])[CH3:3].C(Cl)(=O)C([Cl:32])=O>C(Cl)Cl.CN(C)C=O>[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:8]([Cl:32])=[O:9])([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 19015074HCID 19015074, compound

Product 1

HCID 190153703-(1,1-Dimethylethyl)-4-(tetradecyloxy)benzoyl chlorideYield 9.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 30.0 g of product from Example 32 in 300 ml of methylene chloride and 10 drops of dimethylformamide is added, dropwise, 14.62 g of oxalyl chloride. The reaction is stirred at room temperature for 18 hours and concentrated in vacuo. The residue is dissolved in diethyl ether, filtered through diatomaceous earth and concentrated to give 3.12 g of the desired product as yellow crystals.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue is dissolved in diethyl ether
  3. filtrationfiltered through diatomaceous earth
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-829ac3318e3a496bac62ebdb4d9fe049
Source dataset
uspto-grants-1993_05
Patent number
US05208247

Reaction notes

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