Diethyl Oxalate → HCID 21544774, compound

HRID 1606799Notes

Reaction equation

HRID 1606799 reaction equation
[C:1]([C:4]1[C:23]([OH:24])=[CH:22][CH:21]=[CH:20][C:5]=1[O:6][CH2:7][CH:8]([OH:19])[CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)(=[O:3])[CH3:2].[C:25](OCC)(=O)[C:26]([O:28]CC)=[O:27]>CCOCC>[C:26]([C:25]1[O:24][C:23]2[C:4]([C:1](=[O:3])[CH:2]=1)=[C:5]([O:6][CH2:7][CH:8]([OH:19])[CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)[CH:20]=[CH:21][CH:22]=2)([OH:28])=[O:27]

Participants

4

Reactant 2

HCID 7268Diethyl OxalateHCID 54284726HCID 54284726, compound

Product 1

HCID 21544774HCID 21544774, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 1-(2-acetyl-3-hydroxyphenoxy)-2-hydroxy-3-p-methoxyphenoxypropane (13.3 g) and diethyl oxalate (15 ml) was added to alcohol-free sodium ethoxide (prepared from sodium 3.0 g) in absolute ether (100 ml). The mixture was heated under reflux for 1.5 hours during which time a yellow solid separated. The residue was poured onto ice (100 g) and acidified with a solution of acetic acid (12 ml) in water (80 ml). The ether layer was separated and the aqueous solution was extracted with ether (3 × 25 ml). The combined ethereal layers were evaporated and the residue was dissolved in a mixture of acetic acid (80 ml) and hydrochloric acid (30 ml) and heated under reflux for 1 hour. On pouring into water (1 L) an off white solid was precipitated which was collected and recrystallized from acetic acid to give 1-(2-carboxychromon-5-yloxy)-2-hydroxy-3-p-methoxyphenoxypropane (12.0 g) as a white solid, m.p. 125°-126° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1.5 hours during which time a yellow solid
  3. customseparated
  4. additionThe residue was poured onto ice (100 g)
  5. customThe ether layer was separated
  6. extractionthe aqueous solution was extracted with ether (3 × 25 ml)
  7. customThe combined ethereal layers were evaporated
  8. dissolutionthe residue was dissolved in a mixture of acetic acid (80 ml) and hydrochloric acid (30 ml)
  9. temperatureheated
  10. temperatureunder reflux for 1 hour
  11. additionOn pouring into water (1 L) an off white solid
  12. customwas precipitated which
  13. customwas collected
  14. customrecrystallized from acetic acid

Sources & evidence

ORD record
ord-c419448f685349dca1495e6ee2de4ac9
Source dataset
uspto-grants-1976_04
Patent number
US03953604

Reaction notes

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