Benzene → HCID 19747092, compound

HRID 484292Notes

Reaction equation

HRID 484292 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:14])[C:6](=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[CH:7]=[O:8].[I:15]I.C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[OH:14][C:5]1[C:4]([I:15])=[C:3]([O:2][CH3:1])[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:6]=1[CH:7]=[O:8]

Participants

5

Reactant 3

HCID 241BenzeneHCID 807IodineHCID 1201080HCID 1201080, compound

Product 1

HCID 19747092HCID 19747092, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To the stirred solution of 2.0 g (10.2 mmol) (1.52 mmol) of 4-methoxy-5-nitrosalicylaldehyde and 2.58 g (10.2 mmol) of iodine in 60 ml of carbon tetrachloride, 4.8 g (11.2) mmol) of [bistrifluoroacetoxyl) iodo]benzene was added slowly and then the reaction mixture was stirred for 15 hrs. at RT. To this reaction mixture, 60 ml of hexanes was added and then the formed solid was collected by filtration, washed with hexanes, dilute HCl, water, and dried to give 2.4 g of D. (Yield: 73%): 1H NMR (CDC13) δ12.48 (s, 1H), 9.81 (s, 1H), 8.35 (s, 1H), 4.07 (s, 3H); MS (70 eV) m/e (% relative intensity) M+2 =325 (1.78), M+1 =324 (11) M=323 (100), 293 (41), 276 (51), 262 (11), 120 (8.5), 119 (8.6), 108 (38), 107 (22), 92 (23), 80 (10) 79 (18), 77 (18), 64 (12), 63 (10), 62 (10), 61 (10), 51 (14), 49 (23); IR (nujol) 1660, 1608, 1557, 1512, 1467, 1376, 1312, 1080, 970, 725 cm-1

Workup

  1. customat RT
  2. filtrationthe formed solid was collected by filtration
  3. washwashed with hexanes, dilute HCl, water
  4. customdried
  5. customto give 2.4 g of D

Sources & evidence

ORD record
ord-c34be6bf9a4d4eb0bb2154a24b321dca
Source dataset
uspto-grants-1993_07
Patent number
US05230986

Reaction notes

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