p-Toluenesulfonic acid → HCID 20468638, compound

HRID 1903349Notes

Reaction equation

HRID 1903349 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].[OH:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30]O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CCOCC>[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][CH2:30][CH2:29][O:28][CH2:27][CH2:26][OH:25])=[O:11]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8117Diethylene GlycolHCID 44073Acifluorfen

Product 1

HCID 20468638HCID 20468638, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoic acid (5.6 g, 0.015 mole), 2-hydroxyethyl ether (6.4 g, 0.06 mole) and p-toluenesulfonic acid (200 mg) was heated at 135°-142° C. for 26 hrs. The resulting solution was cooled to room temperature, taken into 400 ml of ether. The ethereal solution was washed three times with water, dried over CaSO4 and concentrated to 4.9 g of a yellowish gum. The gum was chromatographed on silica gel and eluted with hexane-ethyl acetate (90:10); yield 3.4 g of pure 5-hydroxy-3-oxapentyl 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoate as a pale yellow gum; nmr (DMSO-d6) δ 3.56 (s, broad 5H), 3.76 (m, 2H), 4.52 (m, 2H), 7.18-8.40 (m, 6H); ir (CHCl3) 3610, 1750 Cm-1.

Workup

  1. temperaturewas heated at 135°-142° C. for 26 hrs
  2. washThe ethereal solution was washed three times with water
  3. dry with materialdried over CaSO4
  4. concentrationconcentrated to 4.9 g of a yellowish gum
  5. customThe gum was chromatographed on silica gel
  6. washeluted with hexane-ethyl acetate (90:10)

Sources & evidence

ORD record
ord-8d3448664edd40f6ae8f948e6571152d
Source dataset
uspto-grants-1984_03
Patent number
US04435588

Reaction notes

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