Nitric Acid → HCID 22137930, compound

HRID 1827412Notes

Reaction equation

HRID 1827412 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][O:6][C:7]1[CH:8]=[C:9]([OH:13])[CH:10]=[CH:11][CH:12]=1.[N+:17]([O-])([OH:19])=[O:18].O>C(O)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N+:17]([O-:19])=[O:18])=[C:9]([OH:13])[CH:8]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 22137935HCID 22137935, compound

Product 1

HCID 22137930HCID 22137930, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

1.0 g (5 mmol) of 3-(3-fluoro-benzyloxy)-phenol is dissolved in 10 ml acetic acid and cooled to 10°. 0.44 g (5 mmol) of 65% nitric acid is dissolved in 10 ml acetic acid and slowly added to the previous solution. The colored mixture is stirred for 15 min. at 10° and for 2 h at room temperature. 50 ml of water is added and the product extracted 3 times with ethyl acetate. Chromatography (silica gel, dichloromethane/methanol 98:2) yields 0.38 g (32%) of the desired product as a yellow solid. MS: m/e=262.1 (M+−H).

Workup

  1. temperaturecooled to 10°
  2. additionslowly added to the previous solution
  3. extractionthe product extracted 3 times with ethyl acetate

Sources & evidence

ORD record
ord-e809c0d3f4b04ee7a37193ba84367225
Source dataset
uspto-grants-2006_05
Patent number
US07053245B2

Reaction notes

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