Oxalate → HCID 54479874, compound

HRID 1606815Notes

Reaction equation

HRID 1606815 reaction equation
[O-:1][CH2:2][CH3:3].[Na+].[Na].[C:6]([C:9]1[CH:28]=[CH:27][C:12]([O:13][CH2:14][CH:15]([OH:26])[CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=2)=[CH:11][C:10]=1[OH:29])(=[O:8])[CH3:7].[C:30]([O-])(=O)[C:31]([O-])=[O:32]>CCOCC.CS(C)=O.O.C(O)(=O)C.C(O)C>[C:2]([C:3]1[O:29][C:10]2[C:9]([C:6](=[O:8])[CH:7]=1)=[CH:28][CH:27]=[C:12]([O:13][CH2:14][CH:15]([OH:26])[CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=1)[CH:11]=2)([O:32][CH2:31][CH3:30])=[O:1]

Participants

10

Reactant 4

HCID 71081OxalateHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 539131114-[3-(4-Acetyl-3-hydroxyphenoxy)-2-hydroxypropoxy]benzonitrile

Product 1

HCID 54479874HCID 54479874, compound

Reagents, catalysts & solvents 5

HCID 176Acetic AcidSolventHCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a suspension of sodium ethoxide, prepared from sodium (6.0 g) and ethanol (60 ml) in dry ether (400 ml) was added a solution of 1-(4-acetyl-3-hydroxyphenoxy)-2-hydroxy-3-(p-cyanophenoxy) propane (26.2 g) and diethel oxalate (30 ml) in dimethyl sulphoxide (100 ml). After heating under reflux for 2 hours, the suspension was poured onto ice (200 g), acidified with a solution of acetic acid (24 ml) in water (160 ml), and the ether layer separated. The aqueous layer was extracted with ether (3 × 50 ml) and the combined ethereal extracts were evaporated under reduced pressure. The residue was dissolved in ethanol (200 ml) containing concentrated hydrochloric acid (20 drops) and the solution heated under reflux for 1 hour. Removal of the ethanol under reduced pressure gave a solid (24.6 g). On crystallization from ethanol 1-(2 -carbethoxychromon-7-yloxy)-2-hydroxy-3-(p-cyanophenoxy) propane was obtained as white crystals m.p. 170°-172° C.

Workup

  1. temperatureAfter heating
  2. temperatureunder reflux for 2 hours
  3. additionthe suspension was poured onto ice (200 g)
  4. customthe ether layer separated
  5. extractionThe aqueous layer was extracted with ether (3 × 50 ml)
  6. customthe combined ethereal extracts were evaporated under reduced pressure
  7. dissolutionThe residue was dissolved in ethanol (200 ml)
  8. additioncontaining concentrated hydrochloric acid (20 drops)
  9. temperaturethe solution heated
  10. temperatureunder reflux for 1 hour
  11. customRemoval of the ethanol under reduced pressure

Sources & evidence

ORD record
ord-02e3a32a6dbd4310b7fb29de11c5f74a
Source dataset
uspto-grants-1976_04
Patent number
US03953604

Reaction notes

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