Methanol → 2-(4-Hydroxy-2-oxo-2H-chromen-3-ylmethyl)-benzoic acid methyl ester

HRID 857529Notes

Reaction equation

HRID 857529 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][C:4](=[O:12])[C:3]=1[CH2:13][C:14]1[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=1[C:16]([OH:18])=[O:17].S(=O)(=O)(O)O.[CH3:28]O>O>[CH3:28][O:17][C:16](=[O:18])[C:15]1[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=1[CH2:13][C:3]1[C:4](=[O:12])[O:5][C:6]2[C:11]([C:2]=1[OH:1])=[CH:10][CH:9]=[CH:8][CH:7]=2

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 547064482-(4-Hydroxy-2-oxo-2H-chromen-3-ylmethyl)-benzoic acid

Product 1

HCID 546903222-(4-Hydroxy-2-oxo-2H-chromen-3-ylmethyl)-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2-(4-Hydroxy-2-oxo-2H-chromen-3-ylmethyl)-benzoic acid in MeOH with a catalytic amount of conc. sulfuric acid was heated to reflux for 5 hours, cooled to room temperature, diluted with water and extracted with EtOAc. The organic layer was dried over MgSO4 and conc. in vacuo to give 2-(4-Hydroxy-2-oxo-2H -chromen-3-ylmethyl)-benzoic acid methyl ester as white solid. MS: 309[M−H].

Workup

  1. temperatureto reflux for 5 hours
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over MgSO4 and conc. in vacuo

Sources & evidence

ORD record
ord-ac56853b87e5458db4bd07a22d08c04a
Source dataset
uspto-grants-2006_12
Patent number
US07145020B2

Reaction notes

Loading…