Acetic Acid → Methyl 2,6-dihydroxy-3-nitrobenzoate

HRID 1375674Notes

Reaction equation

HRID 1375674 reaction equation
[N+:1]([O-:4])(O)=[O:2].[OH:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]([OH:15])[C:7]=1[C:8]([O-:10])=[O:9].[C:16](O)(=O)C>>[OH:5][C:6]1[C:14]([N+:1]([O-:4])=[O:2])=[CH:13][CH:12]=[C:11]([OH:15])[C:7]=1[C:8]([O:10][CH3:16])=[O:9]

Participants

4

Reactant 3

HCID 176Acetic Acid2×HCID 944Nitric AcidHCID 178524827HCID 178524827, compound

Product 1

HCID 69508249Methyl 2,6-dihydroxy-3-nitrobenzoate

Procedure

1M HNO3 in acetic acid (10 mL, 10.0 mmol) was added dropwise to a solution of 2,6-dihydroxybenzoate (1.68 g, 10.0 mmol) in acetic acid (10 mL) at ambient temperature. The reaction mixture was stirred for 2 hours. The precipitant was filtered and washed with water and acetone, dried to provide the titled compound (1.08 g). MS (ESI(−)) m/e 212 (M−H)+; 1H NMR (300 MHz, DMSO-d6) δ 11.71(bs, 1H), 10.93 (bs, 1H), 8.04 (d, J=9.5 Hz, 1H), 6.60(d, J=9.5 Hz, 1H).

Workup

  1. filtrationThe precipitant was filtered
  2. washwashed with water and acetone
  3. customdried

Sources & evidence

ORD record
ord-2bd30559a4b744059ac8e7b77e26ca21
Source dataset
uspto-grants-2007_01
Patent number
US07169797B2

Reaction notes

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