Nitric Acid → (2-Nitro-4-trifluorobenzyl)acetic acid

HRID 726934Notes

Reaction equation

HRID 726934 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1.[N+:15]([O-])([OH:17])=[O:16]>S(=O)(=O)(O)O>[N+:15]([C:5]1[CH:4]=[C:3]([C:2]([F:13])([F:14])[F:1])[CH:8]=[CH:7][C:6]=1[CH2:9][C:10]([OH:12])=[O:11])([O-:17])=[O:16]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 118342(alpha,alpha,alpha-Trifluoro-4-tolyl)acetic acid

Product 1

HCID 74433(2-Nitro-4-trifluorobenzyl)acetic acid

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a cooled (0°) solution of 4-trifluoromethylphenylacetic acid (550 g; 1.45 mol) in sulfuric acid (2.0 L) was added, over 1.5 hours, nitric acid (90%; 300 mL) at such a rate as to maintain the temperature between 0° and 5° C. The solution was stirred for 15 minutes, then poured into ice water (17 L). The solid that separated was collected on a filter, washed with water (2 times with 2.5 L, by resuspension), then dissolved in ether (3.0 L). The ethereal solution was washed with water (2 times with 1.0 L), dried, then concentrated in vacuo. The last traces of water were removed by co-distillation with ethanol (500 mL). Yield: 588.2 g (96.4%). The material was suitable for further transformation. Additional product (116.6 g) was obtained from a scouting run.

Workup

  1. additionwas added, over 1.5 hours
  2. customThe solid that separated
  3. customwas collected on a filter
  4. washwashed with water (2 times with 2.5 L, by resuspension)
  5. dissolutiondissolved in ether (3.0 L)
  6. washThe ethereal solution was washed with water (2 times with 1.0 L)
  7. customdried
  8. concentrationconcentrated in vacuo
  9. customThe last traces of water were removed by co-distillation with ethanol (500 mL)

Sources & evidence

ORD record
ord-6346955a8af94ee5bf5ae944f013d05b
Source dataset
uspto-grants-1998_01
Patent number
US05711966

Reaction notes

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