Trifluoroacetic anhydride → 7-Nitro-1-tetralone

HRID 1586919Notes

Reaction equation

HRID 1586919 reaction equation
[C:1]1(=[O:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[N+:25]([O-])([O-:27])=[O:26].[NH4+]>C(Cl)Cl>[N+:25]([C:8]1[CH:9]=[C:10]2[C:5]([CH2:4][CH2:3][CH2:2][C:1]2=[O:11])=[CH:6][CH:7]=1)([O-:27])=[O:26]

Participants

5

Reactant 3

HCID 9845Trifluoroacetic anhydrideHCID 107241-TetraloneHCID 22985Ammonium nitrate

Product 1

HCID 384457-Nitro-1-tetraloneYield 41.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

14.62 g of 1-tetralone in 45 ml of methylene chloride were treated with 29.3 ml of trifluoroacetic anhydride and 8.40 g of ammonium nitrate while cooling with ice/NaCl. After 18 hours the mixture was poured cautiously into an ice/conc. NaOH solution and extracted with diethyl ether. The organic phase was washed in succession with soda solution and NaCl solution, dried and evaporated. Flash chromatography on silica gel (hexane/ethyl acetate=9/2) followed by recrystallization from hexane/ethyl acetate (1/1) yielded 7.87 g of 7-nitro-1-tetralone as brownish crystals of m.p. 104°-105° C.

Workup

  1. extractionNaOH solution and extracted with diethyl ether
  2. washThe organic phase was washed in succession with soda solution and NaCl solution
  3. customdried
  4. customevaporated
  5. customFlash chromatography on silica gel (hexane/ethyl acetate=9/2) followed by recrystallization from hexane/ethyl acetate (1/1)

Sources & evidence

ORD record
ord-063a742b3f3b4b9db1cceebbc7fb3a04
Source dataset
uspto-grants-1993_06
Patent number
US05216148

Reaction notes

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