Methanol → Methyl 3-hydroxy-5-nitrobenzoate

HRID 1644619Notes

Reaction equation

HRID 1644619 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH3:19]O>>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[C:5]([O:7][CH3:19])=[O:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 8203933-Hydroxy-5-nitrobenzoic acid

Product 1

HCID 239344Methyl 3-hydroxy-5-nitrobenzoate

Procedure

To a clean, dry 100 mL round bottom flask is added 3-hydroxy-5-nitrobenzoic acid (1 g, 5.5 mmole, 1 eq) followed by 10 mL methanol and 2 mL of concentrated sulfuric acid. The exothermic reaction mixture reached 60° C. prior to cooling to room temperature. The reaction mixture was stirred for 18 h prior to partitioning between ethyl acetate and water. After extraction, the organic layer was dried over magnesium sulfate, filtered and evaporated. A white solid product was obtained (1 g, 100%). Calc'd for C8H7NO5; m/z (M+H+)=198; found 198.

Workup

  1. customTo a clean, dry 100 mL round bottom flask
  2. customreached 60° C.
  3. customto partitioning between ethyl acetate and water
  4. extractionAfter extraction
  5. dry with materialthe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customA white solid product was obtained (1 g, 100%)

Sources & evidence

ORD record
ord-793ab0353477427ebb40bb09735bee9b
Source dataset
uspto-grants-2012_02
Patent number
US08124617B2

Reaction notes

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