Chloroacetyl chloride → HCID 20468612, compound

HRID 1903350Notes

Reaction equation

HRID 1903350 reaction equation
[Cl:1][C:2]1[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[CH:23][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:20]([O-:22])=[O:21])=[C:9]([CH:19]=1)[C:10]([O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][OH:18])=[O:11].C(N(CC)CC)C.[Cl:38][CH2:39][C:40](Cl)=[O:41]>CCOCC>[Cl:1][C:2]1[CH:26]=[C:25]([C:27]([F:28])([F:29])[F:30])[CH:24]=[CH:23][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:20]([O-:22])=[O:21])=[C:9]([CH:19]=1)[C:10]([O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][C:40](=[O:41])[CH2:39][Cl:38])=[O:11]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 20468638HCID 20468638, compound

Product 1

HCID 20468612HCID 20468612, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

5-Hydroxy-3-oxapentyl 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoate (4 g, 0.009 mole) and triethylamine (2 ml) were dissolved in 200 ml of anhydrous ether in a 500 ml round-bottomed flask. Chloroacetyl chloride (5 g, 0.44 mole) was added dropwise. The solution was held at reflux for 4.5 hrs. A large amount of salt precipitated. The ether solution was washed two times with sodium bicarbonate and three times of water, dried over CaSO4 and concentrated to 3.6 g 5-(chloroacetoxy)3-oxapentyl 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoate as a gum; nmr (CDCl3) δ 3.62-3.93 (m, 4H), 4.09 (s, 3H), 4.27-4.66 (m, 4H), 6.96-8.22 (m, 6H); ir (CHCl3) 1754, 1768 Cm-1.

Workup

  1. temperatureat reflux for 4.5 hrs
  2. customA large amount of salt precipitated
  3. washThe ether solution was washed two times with sodium bicarbonate and three times of water
  4. dry with materialdried over CaSO4
  5. concentrationconcentrated to 3.6 g 5-(chloroacetoxy)3-oxapentyl 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoate as a gum

Sources & evidence

ORD record
ord-243bdaf0cebf4463b173ccfb66dd9ed6
Source dataset
uspto-grants-1984_03
Patent number
US04435588

Reaction notes

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