2-Methyl-2-nitro-1-propanol → HCID 53654344, compound

HRID 1759125Notes

Reaction equation

HRID 1759125 reaction equation
[Cl:1][C:2]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:14]([O-:16])=[O:15])=[C:9]([CH:13]=1)[C:10](Cl)=[O:11].[CH3:25][C:26]([N+:30]([O-:32])=[O:31])([CH3:29])[CH2:27][OH:28].C(N(CC)CC)C>CC(C)=O>[Cl:1][C:2]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:14]([O-:16])=[O:15])=[C:9]([CH:13]=1)[C:10]([O:28][CH2:27][C:26]([CH3:29])([N+:30]([O-:32])=[O:31])[CH3:25])=[O:11]

Participants

5

Reactant 3

HCID 64422-Methyl-2-nitro-1-propanolHCID 8471TriethylamineHCID 30177655-(2-Chloro-4-(trifluoromethyl)phenoxy)-2-nitrobenzoyl chloride

Product 1

HCID 53654344HCID 53654344, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent3×

Procedure

To a stirred solution of 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoyl chloride (3.8 g, 0.01 mole) in acetone (10 ml) was added 2-methyl-2-nitropropanol (1.19 g, 0.01 mole) in acetone (10 ml) followed by triethylamine (1.01 g, 0.01 mole) in acetone (5 ml). The temperature rose and a white precipitate formed. The reaction was heated to reflux for 2.5 hours and then stirred overnight at room temperature. After dilution with water (75 ml), the solution was extracted twice with methylene chloride (25 ml @). The organic solution was then washed with 5% sodium hydroxide and finally with a brine solution. The dried solution was concentrated to give an amber oil 2.83 g.

Workup

  1. customa white precipitate formed
  2. temperatureThe reaction was heated
  3. temperatureto reflux for 2.5 hours
  4. extractionAfter dilution with water (75 ml), the solution was extracted twice with methylene chloride (25 ml @)
  5. washThe organic solution was then washed with 5% sodium hydroxide and finally with a brine solution
  6. concentrationThe dried solution was concentrated

Sources & evidence

ORD record
ord-210860e949c64b80a31e83ca745ccf47
Source dataset
uspto-grants-1982_07
Patent number
US04339268

Reaction notes

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