Nitric Acid → 1,1,1,3,3,3-hexafluoro-2-(3-nitrophenyl)propan-2-ol

HRID 429404Notes

Reaction equation

HRID 429404 reaction equation
[N+:1]([O-:4])(O)=[O:2].[F:5][C:6]([F:20])([F:19])[C:7]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([OH:12])[C:8]([F:11])([F:10])[F:9]>>[F:5][C:6]([F:19])([F:20])[C:7]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([N+:1]([O-:4])=[O:2])[CH:18]=1)([OH:12])[C:8]([F:9])([F:11])[F:10]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 69748alpha,alpha-Bis(trifluoromethyl)benzyl alcohol

Product 1

HCID 2795821,1,1,3,3,3-hexafluoro-2-(3-nitrophenyl)propan-2-ol

Conditions

Temperature
0 °C

Procedure

Fuming nitric acid (90%, 5 mL) was added drop wise to 1,1,1,3,3,3-hexafluoro-2-phenyl-2-propanol (4.2 mL, 25 mmol) in concentrated suifliic acid (15 mL) at 0° C. The mixture was stirred at 0° C. for 30 minutes, and at room temperature for 2 hours. Then it was poured into ice water. The solid was fitered, washed with sodium bicarbonate solution, water, and hexane, and dried to give 6.2 g of 1-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]-3-nitrobenzene. 1H NMR (CDCl3): δ 8.66 (s, 1H), 8.38 (d, J=8 Hz, 1H), 8.06 (d, J=8 Hz, 1H), 7.69 (t, J=8 Hz, 1H), 3.66 (bs, 1H). MS (EI) m/z 289 (M+).

Workup

  1. waitat room temperature for 2 hours
  2. washwashed with sodium bicarbonate solution, water, and hexane
  3. customdried

Sources & evidence

ORD record
ord-9cf847faa51f4e69b23d0f16842fe363
Source dataset
uspto-grants-2001_11
Patent number
US06316503B1

Reaction notes

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