Sulfuric Acid → 2-(Acetyloxy)-5-nitrobenzoic acid

HRID 1583250Notes

Reaction equation

HRID 1583250 reaction equation
[N+:1]([C:4]1[CH:12]=[C:8]([C:9]([OH:11])=[O:10])[C:7]([OH:13])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:14](OC(=O)C)(=[O:16])[CH3:15].S(=O)(=O)(O)O>>[C:14]([O:13][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][C:8]=1[C:9]([OH:11])=[O:10])(=[O:16])[CH3:15]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 73185-Nitrosalicylic acidHCID 7918Acetic Anhydride

Product 1

HCID 52112942-(Acetyloxy)-5-nitrobenzoic acid

Conditions

Temperature
55 °C

Procedure

A mixture of 5-nitrosalicyclic acid (5 g), acetic anhydride (13 ml) and sulfuric acid (0.3 ml) was heated at 55° C. for 10 minutes. After the solution was removed from the hot water bath and stirred at room temperature for 1 hour it was poured into water (200 ml). The mixture was stirred for 10 minutes and filtered. The solid was stirred with water (100 ml), filtered by suction and air dried to give the title compound, m.p. ca, 165°-168° C.

Workup

  1. customAfter the solution was removed from the hot water bath
  2. additionwas poured into water (200 ml)
  3. stirringThe mixture was stirred for 10 minutes
  4. filtrationfiltered
  5. stirringThe solid was stirred with water (100 ml)
  6. filtrationfiltered by suction and air
  7. customdried

Sources & evidence

ORD record
ord-eeed9ef5058f473baf1a326cb8a73aa7
Source dataset
uspto-grants-1985_11
Patent number
US04551279

Reaction notes

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