Formaldehyde → HCID 86590040, compound

HRID 857522Notes

Reaction equation

HRID 857522 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])[CH:3]=1.C=O.[CH3:15][C:16]1(C)O[C:21](=O)[CH2:20][C:18](=[O:19])[O:17]1.C([O-])(=O)C.[NH4+]>C(O)C>[CH2:16]([O:17][C:18](=[O:19])[CH2:20][CH2:21][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)[CH3:15]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 517165Ammonium AcetateHCID 546829304-Hydroxycoumarin

Product 1

HCID 86590040HCID 86590040, compoundYield 37.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-hydroxy-chromen-2-one (2.0 g), aqueous formaldehyde (37%, 0.37 g), Meldrum's acid (1.77 g) and ammonium acetate (0.95 g) in ethanol (75 mL) was heated to reflux for 6 hours, then cooled to room temperature. The reaction mixture was conc. in vacuo to give the crude as yellow oil, which was purified by column chromatography to provide 3-(4-Hydroxy-2-oxo-2H-chromen-3-yl)-propionic acid ethyl ester as colorless oil (1.2 g).

Workup

  1. temperatureto reflux for 6 hours
  2. customto give the crude as yellow oil, which
  3. customwas purified by column chromatography

Sources & evidence

ORD record
ord-5e3364ca83e343078d6d4cd7929dca28
Source dataset
uspto-grants-2006_12
Patent number
US07145020B2

Reaction notes

Loading…