Nitric Acid → HCID 18973898, compound

HRID 2395003Notes

Reaction equation

HRID 2395003 reaction equation
[N+:1]([O-:4])([OH:3])=[O:2].[OH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][CH2:13][CH2:14][C:15]1[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=1>C(OC(=O)C)(=O)C>[OH:5][C:6]1[C:11]([N+:1]([O-:4])=[O:2])=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:23][CH:24]=1.[OH:5][C:6]1[CH:11]=[CH:10][C:9]([N+:1]([O-:3])=[O:2])=[CH:8][C:7]=1[CH2:12][CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:23][CH:24]=1

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 18973735Methyl 4-(3-(2-hydroxyphenyl)propyl]benzoate

Product 2

HCID 18973898HCID 18973898, compoundHCID 18974113HCID 18974113, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent2×

Procedure

Nitric acid (15M, 3.13 ml) was added to acetic anhydride 12.52 ml) at 0° C. and the mixture stirred for 15 minutes, then added to a stirred solution of methyl 4-[3-(2-hydroxyphenyl)-propyl]benzoate (12.89 g) in acetic anhydride (300 ml) at 0° C. and stirred for 18 hours. The solvent was evaporated and the resulting yellow oil purified by chromatography on silica gel using ethyl acetate: hexane (1:9 to 1:1 gradient) as eluant to give methyl 4-[3-(2-hydroxy-3-nitrophenyl)propyl]benzoate (5.4 g) and methyl 4-[3-(2-hydroxy-5-nitrophenyl)propyl]benzoate (7.5 g).

Workup

  1. stirringstirred for 18 hours
  2. customThe solvent was evaporated
  3. customthe resulting yellow oil purified by chromatography on silica gel

Sources & evidence

ORD record
ord-f90ccc39469744be94f8a5e8ae0ad2d4
Source dataset
uspto-grants-1998_09
Patent number
US05811459

Reaction notes

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