Ethylene Glycol → HCID 57585939, compound

HRID 547632Notes

Reaction equation

HRID 547632 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][C:10]=2[Cl:17])=[CH:4][C:3]=1[N+:18]([O-:20])=[O:19].[CH2:21](O)[CH2:22][OH:23].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:17][C:10]1[CH:11]=[C:12]([CH:13]2[O:23][CH2:22][CH2:21][O:14]2)[CH:15]=[CH:16][C:9]=1[O:8][C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[C:3]([N+:18]([O-:20])=[O:19])[CH:4]=1

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 57585846HCID 57585846, compound

Product 1

HCID 57585939HCID 57585939, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-[(4-Amino-3-nitrophenyl)oxy]-3-chlorobenzaldehyde (1.16 g, 5.3 mmol), ethylene glycol (5 ml) and p-toluenesulfonic acid (50 mg) in 150 mL of toluene was heated at 120 degrees centigrade with a Dean-Stark trap for 24 hours. The reaction mixture was diluted with ethyl acetate and washed twice with 1N NaOH. The organic layer was dried over MgSO4 and concentrated to give 4-{[2-chloro-4-(1,3-dioxolan-2-yl)phenyl]oxy}-2-nitroaniline. (M+1) 336.9, 2.60 min (LC/MS method B)

Workup

  1. washwashed twice with 1N NaOH
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-afc9fd5a201445f0aa5f8beacdc1768f
Source dataset
uspto-grants-2011_05
Patent number
US07939528B2

Reaction notes

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