Nitric Acid → 2-(4,5-Dichloro-2-nitrophenyl)acetic acid

HRID 1380870Notes

Reaction equation

HRID 1380870 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[N+:13]([O-])([OH:15])=[O:14]>>[Cl:8][C:7]1[C:2]([Cl:1])=[CH:3][C:4]([CH2:9][C:10]([OH:12])=[O:11])=[C:5]([N+:13]([O-:15])=[O:14])[CH:6]=1

Participants

3

Reactant 2

HCID 944Nitric Acid2×HCID 798743,4-Dichlorophenylacetic acid

Product 1

HCID 2441982-(4,5-Dichloro-2-nitrophenyl)acetic acid

Procedure

Here, 3,4-dichlorophenylacetic acid (66.7 g, 0.325 mol) is added in batches, with stirring at 5° C., to a mixture of fuming nitric acid (600 ml) and concentrated nitric acid (300 ml). The mixture is stirred for one hour while cooling is continued and the solution is allowed to rise to 20° C. over a period of a further 1.5 hours. The reaction mixture is poured onto ice, the precipitate is suction filtered, washed with ice water until neutral and then dried. Yield: 54.2 g. Mp: 119°-120° C.

Workup

  1. temperaturewhile cooling
  2. waitto rise to 20° C. over a period of a further 1.5 hours
  3. additionThe reaction mixture is poured onto ice
  4. filtrationfiltered
  5. washwashed with ice water until neutral and
  6. customthen dried

Sources & evidence

ORD record
ord-0cd39d5a0c7049c0b3fe595270fe8638
Source dataset
uspto-grants-1986_04
Patent number
US04584293

Reaction notes

Loading…