3-Hydroxybenzoic Acid → HCID 178420834, compound

HRID 1793753Notes

Reaction equation

HRID 1793753 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1>C(O)C>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O-:7])=[O:6].[NH2+:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 74203-Hydroxybenzoic AcidHCID 8083Morpholine2×

Product 1

HCID 178420834HCID 178420834, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a conical flask, cold absolute ethanol (ca. 40 ml) was added to 99% pure 3-hydroxybenzoic acid (1.8495 g; 13.39 mmol). Dissolution of the acid was achieved at room temperature by constant stirring. Morpholine (1.1653 g, 13.39 mmol) was added dropwise to the acid solution. The reaction was exothermic and some white fumes were observed; the turbid white solution of the acid turned yellow on addition of the colourless morpholine. The opening of the conical flask was covered with parafilm which was then punctured to allow slow evaporation of the solvent at room temperature. Transparent white polyhedral crystals of morpholinium 3-hydroxybenzoate were formed within 24 hrs. The crystals were filtered and washed with small aliquots of cold ethanol. Yield >70% (not optimised).

Workup

  1. dissolutionDissolution of the acid
  2. customwas achieved at room temperature by constant stirring
  3. customevaporation of the solvent at room temperature

Sources & evidence

ORD record
ord-07f9970c50e64af1ab131f98a6014d5c
Source dataset
uspto-grants-2006_07
Patent number
US07081984B1

Reaction notes

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