1-Chloro-2-nitrobenzene → HCID 54500705, compound

HRID 1463434Notes

Reaction equation

HRID 1463434 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:17])=[CH:9][C:10]2[CH:15]=[CH:14][C:13](O)=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.Cl[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[N+:25]([O-:27])=[O:26].[C:28](=[O:31])([O-])[O-].[K+].[K+]>CN(C)C=O>[N+:25]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:17])=[CH:9][C:10]2[CH:15]=[CH:14][C:13]([O:31][C:28]3[CH:22]=[CH:23][CH:24]=[CH:19][C:20]=3[N+:25]([O-:27])=[O:26])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1)([O-:27])=[O:26]

Participants

5

Reactant 3

HCID 69451-Chloro-2-nitrobenzeneHCID 11430Potassium CarbonateHCID 6566934,4'-Dihydroxy-alpha-methylstilbene2×

Product 1

HCID 54500705HCID 54500705, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4,4'-Dihydroxy-alpha-methylstilbene (22.6 grams, 0.20 hydroxyl equivalent) from Example 1-B, o-chloronitrobenzene (39.4 grams, 0.25 mole), -325 mesh anhydrous potassium carbonate (34.5 grams, 0.25 mole) and N,N-dimethylformamide (200 mililiters) are added to a reactor and stirred under a nitrogen atmosphere with heating to 130 deg. C. After 9 hours at the 130 deg. C. temperature, high pressure liquid chromatographic analysis demonstrates that complete conversion of the 4,4'-dihydroxy-alpha-methylstilbene to a single major product has occurred. At this time, the reaction slurry is cooled to room temperature (24 deg. C.), filtered, then rotary evaporated to a constant weight of 53.6 grams of reddish brown colored liquid product.

Workup

  1. additionare added to a reactor
  2. temperaturewith heating to 130 deg. C
  3. filtrationfiltered
  4. customrotary evaporated to a constant weight of 53.6 grams of reddish brown colored liquid product

Sources & evidence

ORD record
ord-f8ca7379373b4987839db5290546192a
Source dataset
uspto-grants-1994_04
Patent number
US05300594

Reaction notes

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