Water → HCID 54216192, compound

HRID 1759126Notes

Reaction equation

HRID 1759126 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]([OH:12])=[O:11].[N+:25]([CH:28]([CH3:31])[CH2:29]O)([O-:27])=[O:26].S(=O)(=O)(O)O.O>C1C=CC=CC=1>[Cl:1][C:2]1[CH:20]=[C:19]([C:21]([F:22])([F:23])[F:24])[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:12][CH2:29][CH:28]([N+:25]([O-:27])=[O:26])[CH3:31])=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 44073AcifluorfenHCID 921872-Nitropropan-1-ol

Product 1

HCID 54216192HCID 54216192, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A stirred mixture of 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid (50 g, 0.139 mole), 2-nitropropanol (13.2 g, 0.126 mole) and conc. sulfuric acid (1 ml) in benzene (500 ml) was heated to reflux for 24 hours, during which time water (1.9 g) was removed via a Dean Stark trap. The solvent was stripped under reduced pressure and the residue poured into water (700 ml). The product was extracted into ether, which was washed with water and then with 5% sodium bicarbonate. The dried ether solution was concentrated to give 23.2 g of an amber oil which slowly solidified to a tacky semi-solid.

Workup

  1. temperaturewas heated
  2. customwas removed via a Dean Stark trap
  3. additionthe residue poured into water (700 ml)
  4. extractionThe product was extracted into ether, which
  5. washwas washed with water
  6. concentrationThe dried ether solution was concentrated

Sources & evidence

ORD record
ord-02055ba4c5824ce184d44962d73ba440
Source dataset
uspto-grants-1982_07
Patent number
US04339268

Reaction notes

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