HCID 67044336, compound → HCID 67044746, compound

HRID 2261963Notes

Reaction equation

HRID 2261963 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:19]=[CH:18][CH:17]=[CH:16][C:11]=2[C:12]([O:14]C)=[O:13])=[CH2:9])=[CH:4][C:3]=1[N+:20]([O-:22])=[O:21]>CO.[OH-].[Na+]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:19]=[CH:18][CH:17]=[CH:16][C:11]=2[C:12]([OH:14])=[O:13])=[CH2:9])=[CH:4][C:3]=1[N+:20]([O-:22])=[O:21]

Participants

4

Reactant 1

HCID 67044336HCID 67044336, compound

Product 1

HCID 67044746HCID 67044746, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

Methyl 2-[1-(4-chloro-3-nitrophenyl)ethenyl]benzoate (0.95 g, 3.0 mmol) was suspended in methanol (45 mL) and 2N sodium hydroxide (100 mL), and stirred at 65° C. for two hours. The reaction mixture was concentrated and acidified to pH of 4, and then extracted with ethyl acetate (3×50 mL). The combined extract was washed with water (100 mL), brine solution (100 mL), dried over sodium sulfate, filtered and concentrated to give 2-[1-(4-chloro-3-nitrophenyl)ethenyl]benzoic acid (0.81 g, 2.7 mmol, 90% yield). 1H NMR (400 MH, CDCl3): 7.92-7.91 (d, 1H), 7.85-7.83 (dd 1H), 7.70-7.67 (d, 1H), 7.66-7.62 (dt, 1H), 7.54-7.50 (dt, 1H), 7.38-7.35 (m, 2H), 5.93 (s, 1H), 5.37 (s, 1H); MS (EI) for C15H10ClNO4: 302 (M−).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. extractionThe combined extract
  4. washwas washed with water (100 mL), brine solution (100 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1e0352ef3c894014b79fbb279e69e09f
Source dataset
uspto-grants-2010_12
Patent number
US07846959B2

Reaction notes

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