Methyl Salicylate → HCID 178511424, compound

HRID 276146Notes

Reaction equation

HRID 276146 reaction equation
[C:1]([O:10]C)(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[CH2:12]([OH:19])[C:13]([NH2:18])([CH2:16][OH:17])[CH2:14][OH:15]>CN(C=O)C.O>[C:1]([O-:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[CH2:12]([OH:19])[C:13]([NH2:18])([CH2:16][OH:17])[CH2:14][OH:15]

Participants

5

Reactant 2

HCID 4133Methyl SalicylateHCID 6503Tris(hydroxymethyl)aminomethane

Product 1

HCID 178511424HCID 178511424, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Methyl salicylate (2.3g, 15.1 mmole) was reacted with Tris (14.8 g, 120.8 mmole) in DMF (182 ml) and water (121 ml) at pH 9.0 and 60° C. for 48 h. The formation of the title product (Rt 3.95) from methyl salicylate (Rt 7.66) was monitored by HPLC (System A) until the reaction stopped at 75% of completion. The mixture was then evaporated to dryness under reduced pressure and the sample dissolved in water. The pH was adjusted to 4.5 and the title product purified by preparative HPLC followed by ion exchange chromatography (Amberlite IR63 resin) to give the chromatographically pure salicylate-Tris (3.66, 65% of theoretical).

Sources & evidence

ORD record
ord-5f52080cf52045c0962c7fd99ed35c87
Source dataset
uspto-grants-2002_03
Patent number
US06353124B1

Reaction notes

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