Acetone → HCID 13657069, compound

HRID 745674Notes

Reaction equation

HRID 745674 reaction equation
[Cl:1][C:2]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:13]([O-:15])=[O:14])=[C:9]([CH:12]=1)[CH2:10]Cl.[C:24]([O:34][CH2:35][CH3:36])(=[O:33])[CH:25]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[OH:26].C(N(CC)CC)C.CC(C)=[O:46]>O>[CH2:35]([O:34][C:24]([CH:25]([O:26][C:10](=[O:46])[C:9]1[CH:12]=[C:5]([O:4][C:3]2[CH:16]=[CH:17][C:18]([C:20]([F:23])([F:22])[F:21])=[CH:19][C:2]=2[Cl:1])[CH:6]=[CH:7][C:8]=1[N+:13]([O-:15])=[O:14])[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[O:33])[CH3:36]

Participants

6

Reactant 4

HCID 180Acetone3×HCID 8471TriethylamineHCID 24197Diethyl malateHCID 13090781HCID 13090781, compound

Product 1

HCID 13657069HCID 13657069, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzyl chloride (3.8 g, 0.01 mole) in acetone (10 ml) was successively added diethyl DL malate (1.9 g, 0.01 mole) in acetone (10 ml) and triethylamine (1.01 g, 0.01 mole) in acetone (5 ml). A white precipitate quickly formed. The reaction was heated to reflux for 24 hours. Upon cooling, the reaction was poured in water (75 ml) and extracted twice with methylene chloride (25 ml@). The combined organic extracts were successively washed with 5% sodium hydroxide and brine solutions. The dried solution was stripped of solvent to give 3.5 g of an amber oil.

Workup

  1. customA white precipitate quickly formed
  2. temperatureThe reaction was heated
  3. temperatureto reflux for 24 hours
  4. temperatureUpon cooling
  5. extractionextracted twice with methylene chloride (25 ml@)
  6. washThe combined organic extracts were successively washed with 5% sodium hydroxide and brine solutions

Sources & evidence

ORD record
ord-b14a83937ea54b66b9bb63b80b93e972
Source dataset
uspto-grants-1986_07
Patent number
US04599442

Reaction notes

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